DOCSLIB.ORG

The Synthesis of 2-Methyl Butanal by Reaction of N-Butyl Isocyanide with Secondary-Butylcadmium Bromide, Pt

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
The Synthesis of 2-Methyl Butanal by Reaction of N-Butyl Isocyanide with Secondary-Butylcadmium Bromide, Pt The synthesis of 2-methyl butanal by reaction of n-butyl isocyanide with secondary-butylcadmium bromide, pt. 1 : a study of the reactions between carbon monoxide and the sodium salt of nitroethane, pt. 2 by John M Bruce Jr A THESIS Submitted to the Graduate Committee in partial fulfillment of the requirements for the degree of Master of Science in Chemsitry at Montana State College Montana State University © Copyright by John M Bruce Jr (1949) Abstract: Part I. 2-methyl butanal was prepared by the following sequence of reactions: [Formulas not Captured by OCR] A light yellow liquid was obtained as product. Confirmatory tests were run using small portions of the final product, and close agreement was found to exist between these results and the actual data pertaining to 2-methyl butanal. The 2,4-dinitrophenylhydrazone derivative was prepared from the final product, and its melting point determined. Experimental details of the above procedure ere presented, along with an explanation of the experimental results. Part II A reaction mixture consisting of the sodium salt of nitroethane and nickel carbonyl in a solvent of cyclohexane, was subjected to high pressures of carbon monoxide. This reaction mixture yielded, upon hydrolysis, a substance possessing a solubility which could not readily be accounted for. This substance is not obtained in the absence of nickel carbonyl, or when cyclohexane itself is subjected to carbon monoxide under pressure in the presence of nickel carbonyl. The unidentified substance is decomposed by steam distillation, simple distillation, and vacuum distillation, and cannot be crystallised satisfactorily even at low temperatures. Positive Schiff's and Tollen's tests were obtained by use of the appropriate reagent and the unknown substance. Derivatization of the unidentified material has not been possible. Additional investigation of the unidentified substance is being conducted. Part I, ©B SBWSSIS # S-MIS'SHYS %mmj& S i HBAefIOH OS n-BUflf ISO- OWIBB VIfK #COmA#-I%%leABBID% BBCMim, Paft II. A SfGDY Qf BBB BBAGfIOBS KBfMBBB OARBQP MQB9&%9% AHD %BB SODIGB sutize op mgaoEmAmi. % ',JOBS M> BvBGOB,' A fHBSlS • ’ ; ’ submit to the Graduate Oomslttea ,. partial fulfillment- Of the requirements for the decree of Master of Science in Chemistry a t Montana State. College Approyedt "'I'WWjIlO.' HI.U' Head of Major Department Chairman, Examining Committee ifean^G-H^duate^risioft Bozeman, Montana June 1949 - 2 - TABLE Of CONTENTS Sg- i m I - I . ABSTRACT ........................... 4 I I . INTRODUCTION .................. 5 I I I . theoretical discussion 7 IV. experimental .................. 10 S ilv e r cy en ld e. ........................... 10 n-Butyl leocysntde .......................... 10 Secondsry-butylms»neeIum bromide 11 Secondsry-butylcedmlum bromide. 12 Synthesis of 2-methyl bntenel . 13 Tests of confirmation .................. 14 Preperetlon of the derivative , 16 V. DISCUSSION OP EXPERIMENTAL RESULTS 18 VI. SUMMARY......................................................... 20 PART H . I . ABSTRACT...................................................................... 21 I I . INTRODUCTION...................................................................................................... 22 I I I . THEORETICAL DISCUSSION................................................................................ 23 IV. EXPERIMENTAL ................................................................................ 2? A p p p re tu s ............................................................................................ 27 Preppretlon of the sodium salt of nit roe then# .................. 28 !typical procedure for experimental ru n s ................................. 29 8 9 3 " 3 (Table of Contents ) - 3 - JaS- A. Effect of Variations In Procedure on Yield of Product . 31 (1) E e e t ..............................................................................................................31 (2) Omission o f N ickel C arbonyl.........................................................31 (3) Omission of S a l t ............................................................. 31 (b) Use of Salt containing methyl alcohol........................................ 31 (5) In presence of hydro .............................................................................32 (6) Hydrolysis of run previous to pressuring with carbon monoxide .................................. 32 (?) V a ria tio n s in p r e s s u r e ..................................................................33 B. Attempts at Purification of Layer B ........... 33 (1) D is tilla tio n a t o rd in ary p re s s u re ........................................... 33 (2) Vacuum distillation. ...... ....................................... 3^ (3) Steam distillation .......................................................................... 3^ (h) C ry s ta lliz a tio n a t Low T e m p e ra tu re .............................................35 C. Attempts to Identify Layer B and Prepare Derivatives. 35 (1) Schiff*s end Tollen1 s T est .......................... ..............................35 (2) 2,U-dInltrophenyIhydrazIne and semlcarbazlde hydro­ c h lo rid e .................................. 35 (3) Schiff1 s Base Formation. .................................................................. 36 (b) Acetal formation ....................................................................................3& •(5) O xid atio n .................................................... 36 (6) Reduction .................................. 38 D. A Reaction Involving the Salt of 2-Nitropropene ...........................38 V. DISCUSSION Of EXPERIMENTAL RESULTS............................................... 40 VI. SUMMARY.......................................................................................................................... 42 V II. ACKNOWLEDGMENT.............................................................................................................4-3 V III. LITERATURE CITED AND CONSULTED......................................................................44 — ^4- — I* abstract £zrk I. 2- methy I buteneI wee prepsred by the following sequence of reectlone: H CH1CH2CH2CH2N=C + CH1CH2-IJHCdBr Br H H A light yellow liquid was obtained se product. Confirmatory tests were run using email portions of the final product, end close agreement wee found to exist between these results end the actual data pertaining to 2-methyl butaneI. The 2fb-dinitrophenylhydrezone derivative was pre­ pared from the final product, and Its melting point determined. Experimental details of the above procedure are presented, along with an explanation of the experimental results. - 5 - J I . INTRODUCTION The ieocypnldes, or cerbylemlnee, RNC, exist me colorless liquids, which pre insoluble In weter, end hpve a pp rtlculfrly disagreeable odor. The vapors are very toxic, capable of causing dizziness end vomiting If in­ haled over a sufficient period of time. The cerbylemlnes are very reactive compounds. Some general reactions involving I so cyan idee and other molecules are listed by Nef^ Oilmen^ ^ , and Cohen^^. It has been demonstrated that the Isocyanide group enters into an addition reaction with the Orignerd reagent; it else enters into reactions with sulfur and chlorine at temperatures above IOO0C1 with the formation of HNCS and ENCtCljg, respectively. Furthermore, it adds acid c h lo rid e s to give alkyllm ldo c h lo rid e s, HNiC(Cl)COR. Sachs and Loevy^?) give the complete procedure for the preparation of benzaldehyde by a reaction involving phenylmagnesiua bromide and methyl Ieo- cyanlde. No other aldehydes are reported to have been synthesized by this method. On the baeis of the results obtained from attempted interaction between phenylmagneslum bromide end various alaphatic and aromatic Iso- (o) cyanides. Oilmen and Heckert concluded that only methyl lsocyanide wee of sufficient reactivity to combine with the Orignard reagent. The desirability of developing.the method of Sachs and Loevy into a good aldehyde synthesis is apparent, since aldehydes are the starting materials from which a large number of important compounds may be made. The selection of the orgenocedmlum compound as sn alternative orgsno- m etallie compound was prompted by the conclusions drawn from the experi­ mental work of Oilman and Nelson^ and de Bonneville^. These workers found that the relatively lower reactivity of the orgpnocadmium compounds caused the arresting of subsequent harmful interaction between the products formed during an in itial stage. Inasmuch as organometallic compounds differ generally in degree or rate of reaction, rather than in kind, it was assumed that the organocadmlua compound would add to the ieocyanlde group in a manner similar to that of the Grignard reagent. It was hoped that a single addition product would result from the reaction between the eerbylamine and the organocadmium compound. Oilman and M elson^^ have treated the subject of organometallic compound preparation quite extensively; however, some disagreement exists (<) between these men and Cason J with regard to the stability of organo­ cadmium compounds et elevated temperatures. According to the letter, the organocadmium compounds can be prepared at room temperature without decom­ position of the product, while Gilman and Nelson state that a cooled reaction mixture is necessary to prevent decomposition. Cason's procedure was the one used in the preparation of the organocadmium compounds in thle work. n-Butyl isocyanide was selected
Load more

Recommended publications
  • Pearson-CV-15.Pdf
    A. J. Pearson/C.V. January 2016 Curriculum Vitae Anthony J. Pearson Academic Rank: Rudolph & Susan Rense Professor of Chemistry Birthplace: Kingswinford, England. Citizenship: British; U.S. Naturalized Citizen. Education: University of Leeds, England, B.Sc. Hons. Class 1, 1971, Chemistry. Aston University, England, Ph.D., 1974, Organic Chemistry. Awards & Honors: Akroyd Scholarship (1969), Whytlaw-Gray Prize for Chemistry (1971), and Dawson Prize for Physical Chemistry (1971), University of Leeds. Sir Gilbert Morgan Medal (1973), Society for Chemical Industry, U.K. Science and Engineering Research Council (U.K.) Advanced Fellowship (1977-82). Sigma Xi Research Award (1984), Case Western Reserve University. John S. Diekhoff Award for Distinguished Graduate Teaching (1994), Case Western Reserve University. Visiting Scientist, Chemistry Research Promotion Center, Taipei, Taiwan, R.O.C., May 1990. Visiting Professor, University of Auckland, New Zealand, July/August, 1995. Chairman-Elect, American Chemical Society, Cleveland Section, 1999. Chairman, 2000. Finalist (one of three) for Northern Ohio Live 2001 Award of Achievement in Architecture, with R. Bostwick, N. Distad, K. Kutina, and N. Rushforth, for design of Agnar Pytte Science Center at CWRU. Case Alumni Association, Recognition of Meritorious Service, 2003. Experience: 1963-66 Chemist. Industrial research and analytical laboratories. Albright & Wilson; British Steel; West Midlands Gas Board. Semi-professional musician. 1974-77 Postdoctoral Research Fellow, with Arthur J. Birch. Research School of Chemistry, Australian National University, Canberra, Australia. 1977-82 SERC Advanced Fellow. Cambridge University Chemical Laboratory. 1978-81 Pauline Merz Official Fellow and Lecturer in Chemistry. Girton College, Cambridge University. 1979-81 Tutor. Girton College, Cambridge University. 1982-84 Associate Professor of Chemistry.
    [Show full text]
  • The Direct Electrochemical Synthesis of Selected Group-Iib Organometallic Compounds
    University of Windsor Scholarship at UWindsor Electronic Theses and Dissertations Theses, Dissertations, and Major Papers 1-1-1979 THE DIRECT ELECTROCHEMICAL SYNTHESIS OF SELECTED GROUP-IIB ORGANOMETALLIC COMPOUNDS. AKHTAR OSMAN University of Windsor Follow this and additional works at: https://scholar.uwindsor.ca/etd Recommended Citation OSMAN, AKHTAR, "THE DIRECT ELECTROCHEMICAL SYNTHESIS OF SELECTED GROUP-IIB ORGANOMETALLIC COMPOUNDS." (1979). Electronic Theses and Dissertations. 7187. https://scholar.uwindsor.ca/etd/7187 This online database contains the full-text of PhD dissertations and Masters’ theses of University of Windsor students from 1954 forward. These documents are made available for personal study and research purposes only, in accordance with the Canadian Copyright Act and the Creative Commons license—CC BY-NC-ND (Attribution, Non-Commercial, No Derivative Works). Under this license, works must always be attributed to the copyright holder (original author), cannot be used for any commercial purposes, and may not be altered. Any other use would require the permission of the copyright holder. Students may inquire about withdrawing their dissertation and/or thesis from this database. For additional inquiries, please contact the repository administrator via email ([email protected]) or by telephone at 519-253-3000ext. 3208. 492-33 National Library Bibliothfeque nationale CANADIAN THESES THESES CANADtENNES f l * .of Canada ~ du Canada ON MICROFICHE SUB UJCBOFICHE NAME OF AUTHOR/NOM O f L’AUTEUR. A khtar Osman TITLE OF THEStS/7777?£ O f LA THESE- The direct electrochemical synthesis of selected grouo IIB organonetallic compounds. UNIVERSITY/LW/ VERS/ TE. U niversity of ~Windsor. Windsor ..Ontario DEGREE FOR WHICH THESIS WAS PRESENTED/.
    [Show full text]
  • Synthesis, Properties Characterization and Applications of Various Organobismuth Compounds
    Molecules 2011, 16, 4191-4230; doi:10.3390/molecules16054191 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Review Synthesis, Properties Characterization and Applications of Various Organobismuth Compounds Jingfei Luan *, Lingyan Zhang and Zhitian Hu State Key Laboratory of Pollution Control and Resource Reuse, School of the Environment, Nanjing University, Nanjing 210093, China; E-Mails: [email protected] (L.Z.), [email protected] (Z.H.) * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +86-135-8520-6718; Fax: +86-25-8370-7304. Received: 15 April 2011; in revised form: 9 May 2011 / Accepted: 12 May 2011 / Published: 20 May 2011 Abstract: Organobismuth chemistry was emphasized in this review article due to the low price, low toxicity and low radioactivity characteristics of bismuth. As an environmentally- friendly class of organometallic compounds, different types of organobismuth compounds have been used in organic synthesis, catalysis, materials, etc. The synthesis and property characterization of many organobismuth compounds had been summarized. This review article also presented a survey of various applications of organobismuth compounds in organic transformations, as reagents or catalysts. The reactivity, reaction pathways and mechanisms of reactions with organobismuths were discussed. Less common and limiting aspects of organobismuth compounds were also briefly mentioned. Keywords: organobismuth compounds; synthesis; properties; reagent; catalyst 1. Introduction Organometallic compounds such as organoboron, organotin, organosilicon, organoantimony, organolead, etc. have been widely applied in organic synthesis in the past several decades [1-3]. A number of reports [4-8] on these compounds have mentioned their positive role in a variety of synthetic transformations or polymerizations, acting as reagents or catalysts.
    [Show full text]
  • REGIOCHEMISTRY of DIALKYL CADMIUM ADDITION to Cis- AND
    REGIOCHEMISTRY OF DIALKYL CADMIUM ADDITION TO cis- AND trans-HEXAHYDROPHTHALIC ANHYDRIDES By VASUDHA BALASUBRAMANIAN h Master of Science Pune University Pune,India 1982 Submitted to the Faculty of the Graduate College of the Oklahoma State University in partial fulfillment of the requirements for the Degree of MASTER OF SCIENCE December,l987 Tk~\o() \9~1 'B\1 \ r (.op. d REGIOCHEMISTRY OF DIALKYL CADMIUM ADDITION TO cis- AND trans-HEXAHYDROPHTHALIC ANHYDRIDES Dean of the Graduate College ii 129086"/ ACKNOWLEDGEMENTS I wish to express my gratitude to Dr.E.J.Eisenbraun for his guidance,understanding and encouragement throughout this study. Many thanks also go to Dr.J.P.Devlin and Dr.I.D.Eubanks for serving on my graduate committee. I also wish to thank the members of the faculty and the staff of the Chemistry Department for their assistance during the course of this work. I would also like to thank Mr.Stan Sigle for his help in obtaining NMR spectra. My deepest gratitude to my parents,-for their constant and unstinting love,understanding and support. iii TABLE OF CONTENTS Chapter Page I. INTRODUCTION AND HISTORICAL 1 II. RESULTS AND DISCUSSION 16 III. EXPERIMENTAL ..... 33 cis-2-Acetylcyclohexanecarboxylic Acid (3a). 34 a. Grignard Reaction • . • • . • . 34 b. Methyl Lithium Reaction . 35 c. Synthesis of the Dimethyl Cadmium Reagent . • . • . 37 d. Reaction with Dimethyl Cadmium . 37 trans-2-Acetylcyclohexanecarboxylic Acid (3b). 39 a. Reaction with Dimethyl Cadmium • . • 39 b. Epimerization Reaction . 40 cis-2-Trimethylacetylcyclohexanecarboxylic- .h::::id (~ • • • • • • • • • • • • • • • 41 a. synthesis of the Di-tert-butyl Cadmium Reagent . 42 b. Reaction with Di-tert-butyl Cadmium .
    [Show full text]
  • Advanced Organic Chemistry PART A: Structure and Mechanisms PART B: Reactions and Synthesis Advanced Organic FIFTH Chemistry EDITION
    Advanced Organic FIFTH Chemistry EDITION Part B: Reactions and Synthesis Advanced Organic Chemistry PART A: Structure and Mechanisms PART B: Reactions and Synthesis Advanced Organic FIFTH Chemistry EDITION Part B: Reactions and Synthesis FRANCIS A. CAREY and RICHARD J. SUNDBERG University of Virginia Charlottesville, Virginia 123 Francis A. Carey Richard J. Sundberg Department of Chemistry Department of Chemistry University of Virginia University of Virginia Charlottesville, VA 22904 Charlottesville, VA 22904 Library of Congress Control Number: 2006939782 ISBN-13: 978-0-387-68350-8 (hard cover) e-ISBN-13: 978-0-387-44899-2 ISBN-13: 978-0-387-68354-6 (soft cover) Printed on acid-free paper. ©2007 Springer Science+Business Media, LLC All rights reserved. This work may not be translated or copied in whole or in part without the written permission of the publisher (Springer Science+Business Media, LLC, 233 Spring Street, New York, NY 10013, USA), except for brief excerpts in connection with reviews or scholarly analysis. Use in connection with any form of information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now know or hereafter developed is forbidden. The use in this publication of trade names, trademarks, service marks and similar terms, even if they are not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. 98765432(corrected 2nd printing, 2008) springer.com Preface The methods of organic synthesis have continued to advance rapidly and we have made an effort to reflect those advances in this Fifth Edition.
    [Show full text]
  • Download (6MB)
    STUDIES ON THE GENERATION AND REACTIVITY OF METAL CARBENOIDS A Thesis Presented by Rehan Aqil In Partial Fulfilment of the Requirements for the Award of the Degree of DOCTOR OF PHILOSOPHY OF THE UNIVERSITY OF LONDON Christopher Ingold Laboratories Department of Chemistry University of London London WCIH OAJ September 2002 ProQuest Number: U643094 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. uest. ProQuest U643094 Published by ProQuest LLC(2015). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code. Microform Edition © ProQuest LLC. ProQuest LLC 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 48106-1346 Abstract ABSTRACT This thesis concerns the generation of metal carbenoids, in particular organozinc carbenoids, and their subsequent reactions, such as C-H insertion reactions or cyclopropanation with alkenes. The thesis is divided into three major sections. The introductory chapter presents a comparative review covering metal carbenoid species. The review focuses on how their reactivity is controlled by the metal, the leaving group and by the nature of electron-donating and -withdrawing groups on the carbenoid and finally which type of alkenes give the highest reactivity and yields as a function of these parameters. The results and discussion chapter opens with a brief overview of the organozinc carbenoid chemistry which has been developed within our group.
    [Show full text]
  • University Department of Chemistry B.R.A. Bihar University, Muzaffarpur. Question Bank Subject: Chemistry, Course: B.Sc.(H), Year: Part 1 Paper: II
    University Department of Chemistry B.R.A. Bihar University, Muzaffarpur. Question Bank Subject: Chemistry, Course: B.Sc.(H), Year: Part 1 Paper: II 1.Atomic Structure : 1.What is a blackbody? (a) A body that absorbs all the electromagnetic radiation that falls on it. (b) A body that absorbs only infrared part of the electromagnetic radiation. (c) A body that absorbs only visible part of the electromagnetic radiation. (d) A body that absorbs only microwave part of the electromagnetic radiation. 2.The rate of radiation emitted per unit surface area of a blackbody depends: (a) Only on temperature of materials. (b) Only on the nature of materials. (c) Both (a) & (b) (d)Neither on the temperature nor on the nature of materials. 3.The value of Planck’s constant is: -33 (a)6.626 ×10 J.S (b) 6.626×10-35J.S (c) 6.626×10-34 J.S (d) 6.626×10-23 J.S 4.The relation between energy (E) and frequency (ʋ) of the electromagnetic radiation is: (a)E=hʋ (b)E= ʋ/h (c) E=h/ʋ (d) E=1/hʋ Q 5. The particle nature of the electromagnetic radiation is given by: (a) Planck’s Quantum Theory (b) Heisenberg Uncertainty Principle (c) The De Broglie Hypothesis (d) None Q 6. Heisenberg Uncertainty Principle is applicable to: (a) Macroscopic particles (b) Ideal Gases (c) Real Gases (d) Microscopic particles Q 7. According to Heisenberg Uncertainty Principle: (a) Δx.Δpx ≥ h/4л (b) Δx.Δpx = h/2л (c) Δx.Δpx ≤ h/4л (d) Δx.Δpx = 1/h 8.
    [Show full text]
  • The Reactions of Aliphatic Acid Chlorides Norman 0
    THE REACTIONS OF ALIPHATIC ACID CHLORIDES NORMAN 0 . V . SONNTAG Colgate-Palmolive-Peet Company. Jersey City. New Jersey Received November 16. 1962 CONTENTS I . Introduction .................. ......................................... 238 I1. Scope of the revieL1. ....................................................... 239 I11 . Nomenclature ............................................. IV . Reduction of aliphatic acid chlorides ...................... A . The Rosenmund reduction., ............................................ 245 B . Catalytic hydrogenation .............................................. 247 C . Chemical methods of reduction ....................................... 248 1. With sodium amalgam .......................................... 2 . With metal hydrides ................................................ 249 3 . With other reducing agents ........................................ 251 V . Hydrolysis of aliphatic acid chlorides ....................................... 251 VI . Reaction of aliphatic acid chlorides with ammonia, hydroxylamine, and hy- drazine ................................................................... 258 A . Reaction with ammonia .............................................. 258 1. At low temperatures............................................... 258 2 . At high temperatures ................................................ 265 B . Reaction with hydroxylamine and hydrazine.,........................... 266 VI1. Reaction of aliphatic acid chlorides with amines, substituted amines, and re- lated compounds
    [Show full text]
  • Organometallic Compounds in the Environment
    Organometallic Compounds in the Environment Seco n d ed it io n EditedbyP.J.Craig School of Molecular Sciences, D e Mont f o rt Un iversit y , L eicest er, UK Organometallic Compounds in the Environment Organometallic Compounds in the Environment Seco n d ed it io n EditedbyP.J.Craig School of Molecular Sciences, D e Mont f o rt Un iversit y , L eicest er, UK First Edition published by Longman, 1986. ISBN:0582 46361 0 Copyright © 2003 John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex PO19 8SQ, England Telephone (+44) 1243 779777 Email (for orders and customer service enquiries): [email protected] Visit our Home Page on www.wileyeurope.com or www.wiley.com All Rights Reserved. No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning or otherwise, except under the terms of the Copyright, Designs and Patents Act 1988 or under the terms of a licence issued by the Copyright Licensing Agency Ltd, 90 Tottenham Court Road, London W1T 4LP, UK, without the permission in writing of the Publisher. Requests to the Publisher should be addressed to the Permissions Department, John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex PO19 8SQ, England, or emailed to [email protected], or faxed to (+44) 1243 770620. This publication is designed to provide accurate and authoritative information in regard to the subject matter covered. It is sold on the understanding that the Publisher is not engaged in rendering professional services.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 6,887,736 B2 Nause Et Al
    USOO6887736 B2 (12) United States Patent (10) Patent No.: US 6,887,736 B2 Nause et al. (45) Date of Patent: May 3, 2005 (54) METHOD OF FORMING A P-TYPE GROUP 5,413.959 A 5/1995 Yamamoto et al. I-V SEMCONDUCTOR CRYSTAL LAYER 5,458,085 A * 10/1995 Kondo et al. .............. 148/33.6 ON A SUBSTRATE 5,468,678 A 11/1995 Nakamura et al. 5,603,778 A 2/1997 Sonoda 5,668,395 A * 9/1997 Razeghi...................... 257/441 (75) Inventors: Jeffrey E. Nause, Mableton, GA (US); 5,769,963 A * 6/1998 Fujioka et al. .............. 136/258 Joseph Owen Maciejewski, Mableton, 5,804.4662Y- - -2 A 9f1998 Arao et al. GA (US); Vincente Munne, Norcross, 5863326 A 1/1999 Nause et al. GA (US); Shanthi Ganesan, Smyrna, 5,882,805 A * 3/1999 Higa et al. ..... ... 428/689 GA (US) 5,897,332 A * 4/1999 Hori et al. .................... 438/61 5,900,060 A 5/1999 Nause et al. (73) Assignee: Cermet, Inc., Atlanta, GA (US) (Continued) (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 OTHER PUBLICATIONS U.S.C. 154(b) by 10 days. Minegishi et al, Growth of p-type Zinc Oxide Films by Chemical Vapor Depositions Article, Nov. 1, 1997, L 1453– (21) Appl. No.: 10/422,568 L 1455, vol. 36, Department of Electrical Engineering and (22) Filed: Apr. 23, 2003 Computer Science, Yamanashi University, 4 Takeda, Kofu. 400, Japan. (65) Prior Publication Data Yamamoto et al, Solution Using a Codoping Method to Unipolarity for the Fabrication of p-Type ZnO, Article, Feb.
    [Show full text]
  • LEZ047.Pdf (354.4Kb)
    The solid phase synthesis of tertiary hydroxyesters from symmetrical diacid chlorides using organomanganese reagents l'2 Cltrrono C. LezNopp eNo Vanon Yeorore Department of Chemistry, York Uniuersity, Downsuiew, Ont., Canada M3J I P3 CLtRpono C. Lezuorr and Vnnoa Yeolore. Can. J. Chem. 58, 287 (1980). A l7o crosslinked divinylbenzene-styrene copolymer, incorporating benzyl alcohol groups, was used to monoblock the symme- trical diacid chlorides, CIOC(CHz)oCOCl (where n : 4 and 8). Furtherreaction ofthe polymer-bound monoester monoacid chloride with phenylmanganese iodide or butylmanganese iodide gave their respective polymer-bound tertiary hydroxyesters. Subsequent base cleavage and esterification yielded methyl 6-hydroxy-6,6-diphenylhexanoate, methyl l0-hydroxy-10,10-diphenyldecanoate, methyl 6-butyl-6-hydroxydecanoate, and methyl 10-butyl- l0-hydroxytetradecanoate and some recovered dimethylalkanoates. The reactions ofsome polymer-bound monoester monoacid chlorides with phenylcadmium chloride were also studied. Cunnono C. LezNorr et VARDA YEDIDrn. Can. J. Chem. 58,287 (1980). Onautilis6uncopolymbrestyrbne-divinylbenzbnereticul6i l7oetcontenantdesgroupesalcoolbenzyliquepourbloquerunedes fonctions des dichlorures de diacides sym6triques CIOC(CHu ),COCl (oi n = 4 et 8). La r6action de I'esterainsi obtenu avec I'iodure de phdnylmanganEse ou I'iodure de butylmangandse conduit ir leurs hydroxy-esters tertiaires respectifs fix6s surla 16sine. Le clivage subs6quent par une base suivi d'une est6rification conduit aux compos6s: hydroxy-6 diph6nyl-6,6 hexanoate de m6thyle, hydroxy- l0diph€nyl-10,10 d6canoate de m6thyle, butyl-6 hydroxy-6d6canoate de m6thyle et Ie butyl-10 hydroxy-l0tdtraddcanoate de m6thyle et 6galement ir la r6cupdration de quelques alkanoates de mdthyle. On a dgalement €tudi6 les rdactions de quelques monochlorures d'acideS fix€s sur la 16sine par une liaison ester avec le chlorure de ph6nylcadmium.
    [Show full text]
  • Rearrangement Studies and Novel Reactions of Organocadmium Reagents
    University of New Hampshire University of New Hampshire Scholars' Repository Doctoral Dissertations Student Scholarship Spring 1978 REARRANGEMENT STUDIES AND NOVEL REACTIONS OF ORGANOCADMIUM REAGENTS JAMES GERARD SHELNUT Follow this and additional works at: https://scholars.unh.edu/dissertation Recommended Citation SHELNUT, JAMES GERARD, "REARRANGEMENT STUDIES AND NOVEL REACTIONS OF ORGANOCADMIUM REAGENTS" (1978). Doctoral Dissertations. 1198. https://scholars.unh.edu/dissertation/1198 This Dissertation is brought to you for free and open access by the Student Scholarship at University of New Hampshire Scholars' Repository. It has been accepted for inclusion in Doctoral Dissertations by an authorized administrator of University of New Hampshire Scholars' Repository. For more information, please contact [email protected]. INFORMATION TO USERS This material was produced from a microfilm copy of the original document. While the most advanced technological means to photograph and reproduce this document have been used, the quality is heavily dependent upon the quality of the original submitted. The following explanation of techniques is provided to help you understand markings or patterns which may appear on this reproduction. 1.The sign or "target" for pages apparently lacking from the document photographed is "Missing Page(s)". If it was possible to obtain the missing page(s) or section, they are spliced into the film along with adjacent pages. This may have necessitated cutting thru an image and duplicating adjacent pages to insure you complete continuity. 2. When an image on the film is obliterated with a large round black mark, it is an indication that the photographer suspected that the copy may have moved during exposure and thus cause a blurred image.
    [Show full text]