DOCSLIB.ORG

Modern Gold Catalyzed Synthesis

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Modern Gold Catalyzed Synthesis Edited by A. Stephen K. Hashmi and Dean F. Toste Modern Gold Catalyzed Synthesis Edited by A. Stephen K. Hashmi and F. Dean Toste Modern Gold Catalyzed Synthesis Further Reading Mohr, F. (ed.) Ertl, G., Knözinger, H., Schüth, F., Gold Chemistry Weitkamp, J. (eds.) Highlights and Future Directions Handbook of Heterogeneous 2009 Catalysis ISBN: 978-3-527-32086-8 8 Volumes 2008 Laguna, A. (ed.) ISBN: 978-3-527-31241-2 Modern Supramolecular Gold Chemistry Ding, K., Uozumi, Y. (eds.) Gold-Metal Interactions and Applications Handbook of Asymmetric 2008 Heterogeneous Catalysis 2008 ISBN: 978-3-527-32029-5 ISBN: 978-3-527-31913-8 Dupont, J., Pfeffer, M. (eds.) Palladacycles Synthesis, Characterization and Applications 2008 ISBN: 978-3-527-31781-3 Edited by A. Stephen K. Hashmi and F. Dean Toste Modern Gold Catalyzed Synthesis Wiley-VCH The Editors All books published by are carefully produced. Nevertheless, authors, editors, and pub- Prof. Dr. A. Stephen K. Hashmi lisher do not warrant the information contained in Organisch-Chemisches Institut these books, including this book, to be free of errors. Universität Heidelberg Readers are advised to keep in mind that statements, Im Neuenheimer Feld 270 data, illustrations, procedural details or other items 69120 Heidelberg may inadvertently be inaccurate. Library of Congress Card No.: applied for Prof. F. Dean Toste Department of Chemistry British Library Cataloguing-in-Publication Data University of California A catalogue record for this book is available from the Berkeley, CA 94720-1460 British Library. USA Bibliographic information published by the Deutsche Nationalbibliothek The Deutsche Nationalbibliothek lists this publica- tion in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at http://dnb.d-nb.de. # 2012 Wiley-VCH Verlag & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, micro- film, or any other means – nor transmitted or trans- lated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Print ISBN: 978-3-527-31952-7 ePDF ISBN: 978-3-527-64689-0 ePub ISBN: 978-3-527-64688-3 mobi ISBN: 978-3-527-64687-6 oBook ISBN: 978-3-527-64686-9 Cover Design Formgeber, Eppelheim Typesetting Thomson Digital, Noida, India Printing and Binding betz-druck GmbH, Darmstadt, Germany V Contents List of Contributors XIII 1 Hydrochlorination of Acetylene Catalyzed by Gold 1 Marco Conte and Graham J. Hutchings 1.1 Introduction 1 1.2 Reactions of Alkynes Using Gold Chloride as Catalyst 2 1.3 The Correlation of E 88 with the Activity of Gold for the Hydrochlorination of Acetylene 4 1.3.1 The Initial Correlation 4 1.3.2 Conceptual Developments of the E8 Correlation 5 1.3.3 Further Study of the Correlation of E8 with the Activity of Platinum Group Metals 8 1.3.4 The E8 Correlation Applied to Homogeneous and Nonhomogeneous Gold Nanoalloys 9 þ 1.4 Central Role of Au3 and Regeneration of Au/C Catalysts 12 1.5 Reaction Mechanism of Alkynes Over Au/C Catalysts 14 1.5.1 Effect of the Individual Components of the Reactants to Au/C 14 1.5.2 Reaction of Higher Alkynes Over Au/C 16 1.5.3 Hydrochlorination of 1-hexyne, phenylacetylene, and 2-hexyne Over Au/C Catalyst 17 1.5.4 Computational Studies of the Reaction of Acetylene Over Au/C 21 1.6 Chemical Origin of the E8 Correlation and General Remarks 22 1.7 Commercial Processes and Economic Aspects of Vinyl Chloride Monomer Manufacture 24 References 25 2 Gold-Catalyzed Reduction Reactions 27 Avelino Corma and Pedro Serna 2.1 Introduction 27 2.2 Hydrogenation of Multiple C¼C Bonds. Role of the Gold Oxidation State 28 2.2.1 Introduction 28 VI Contents 2.2.2 First Solid Gold Catalysts: from Extended Au Surfaces to Highly Dispersed Nanoparticles 28 2.2.3 Recent Advances in Supported Gold Chemistry: from Highly Dispersed Nanoparticles to Individual Supported Au Atoms 31 2.2.4 Summary 34 2.3 Hydrogenation of a,b-Unsaturated Aldehydes 34 2.3.1 Introduction 34 2.3.2 Chemistry of Gold Nanoparticles: First Studies and Hypotheses 36 2.3.3 Strong Metal–Support Interactions: Effect of Electronic Transfers and Decoration on the Gold Nanoparticles 37 2.3.4 Effect of Morphological Factors: Size and Shape 38 2.3.5 Summary 39 2.4 Hydrogenation of Substituted Nitroaromatic Compounds 41 2.4.1 Introduction 41 2.4.2 Gold Catalysts for the Production of Substituted Nitro Compounds 42 – 2.4.3 Hydrogenation of NO2 Groups on Gold Catalysts: Reaction Pathway 43 2.4.4 Chemoselectivity of Gold Catalysts for the Hydrogenation 47 of NO2 groups 2.4.5 Activity of Gold Catalysts for the Hydrogenation of NO2 groups 49 2.4.6 Summary 51 References 51 3 Gold-Catalyzed Benzannulations: Asao–Yamamoto Benzopyrylium Pathway 55 Naoki Asao and Yoshinori Yamamoto 3.1 Introduction 55 3.2 Acetylenic Compounds as 2p Systems 56 3.3 Enols as 2p Systems 60 3.4 Enol Ethers as 2p Systems 62 3.5 Benzynes as 2p Systems 63 3.6 Synthesis of Phthalazine Derivatives 64 3.7 Application to the Synthesis of Angucyclinone Antibiotics and Other Applications in Total Synthesis 65 3.8 Copper-Catalyzed Benzannulations 67 3.9 Conclusion 68 References 69 4 Gold-Catalyzed Reactions of Propargyl Esters, Propargyl Alcohols, and Related Compounds 75 Pablo Mauleon and F. Dean Toste 4.1 Introduction and Extent of This Chapter 75 4.2 Propargyl Esters 76 Contents VII 4.2.1 General Mechanistic Considerations 76 4.2.1.1 [2,3]- and [3,3]-Rearrangements 77 4.2.1.2 Reversibility 78 4.2.1.3 Ionization 80 4.2.1.4 Double [2,3]-Rearrangements 83 4.2.2 Reactions Initiated by [2,3]-Rearrangements 85 4.2.2.1 The Rautenstrauch Rearrangement 86 4.2.2.2 Alkene Cyclopropanations 87 4.2.2.3 Enantioselective Transformations After [2,3]-Rearrangements 92 4.2.2.4 Nucleophilic Attack on Gold Carbenoids Generated After [2,3]-Rearrangements 94 4.2.3 Reactions Initiated by [3,3]-Rearrangements 96 4.2.3.1 Nucleophilic Double Bonds 97 4.2.3.2 Triple Bonds 99 4.2.3.3 Aromatic Groups 100 4.2.3.4 Alkyl Groups 100 4.2.3.5 Heteroatoms 102 4.2.3.6 Electrophilic Trapping of Vinyl–Gold Intermediates 103 4.2.3.7 Other Processes 104 4.3 Propargyl Ethers 107 4.3.1 Propargyl Vinyl Ethers 107 4.3.2 Propargyl Alkyl Ethers 110 4.3.3 Other Ether Substitution Patterns 113 4.4 Propargyl Alcohols 115 4.4.1 Alkyne Hydration 115 4.4.2 Meyer–Schuster Rearrangements 115 4.4.3 Nucleophilic Substitution at the Propargylic Position 117 4.4.4 Ring Expansions 117 4.4.5 Other Reactions Involving Propargyl Alcohols 119 4.5 Propargyl Amines 121 4.6 Propargyl Carbonates, Amides, and Carbamates 124 4.7 Other Propargyl Substitution Patterns 127 4.8 Conclusion 129 References 130 5 Intramolecular Hydroarylation of Alkynes 135 Paula de Mendoza and Antonio M. Echavarren 5.1 Introduction 135 5.2 Intramolecular Reactions of Arenes with Alkynes 137 5.3 Intramolecular Reactions of Electron-Rich Heteroarenes with Alkynes 142 5.4 Conclusion and Outlook 148 References 148 VIII Contents 6 Gold–Alkyne Complexes 153 Maria Agostina Cinellu 6.1 Introduction 153 6.2 Description of the M–p-Bond Interaction in Alkene and Alkyne Complexes 154 6.3 Gold(0) Complexes 155 6.4 Gold(I) Complexes 155 6.4.1 Neutral Derivatives 155 6.4.2 Cationic Derivatives 158 6.4.3 p-Complexation of Gold(I) at Metal–Alkynyl Units M–CC–R 164 6.5 Gold(III) complexes 167 6.6 Theoretical Studies 167 References 171 7 Gold–Alkene Complexes 175 Maria Agostina Cinellu 7.1 Introduction 175 7.2 Gold(0) Derivatives 176 7.3 Gold(I) Complexes 176 7.3.1 Neutral Derivatives 176 7.3.1.1 14-Electron Species 176 7.3.1.2 16-Electron Species 178 7.3.2 Cationic Derivatives 181 7.3.2.1 14-Electron Species 181 7.3.2.2 16-Electron Species 186 7.4 Gold(III) Complexes 191 7.5 Theoretical Studies 192 References 196 8 Hydration and Hydroalkoxylation of CC Multiple Bonds 201 J. Henrique Teles 8.1 Historical Perspective 201 8.1.1 Addition of Water to Alkynes 201 8.1.2 Addition of Alcohols to Alkynes 202 8.2 Gold Catalysts 202 8.2.1 First Reports of Gold Catalysts 203 8.2.2 The Discovery of Au(I) Catalysts 204 8.2.2.1 Catalyst Precursors 206 8.2.2.2 The Importance of Chemical Equilibria 208 8.3 Hydration and Hydroalkoxylation of CC Triple Bonds (Alkynes) 209 8.3.1 Effect of Alcohol Structure 209 8.3.2 Addition of Water to Alkynes 211 8.3.3 Addition of Alcohols to Simple Alkynes 215 8.3.4 Reactions Involving Propargylic Alcohols 217 8.3.5 Additions to Homopropargylic Alcohols and Other Alkynols 220 Contents IX 8.3.6 Reactions Involving Propargylic Ethers 224 8.4 Hydration and Hydroalkoxylation of CC Double Bonds (Allenes and Alkenes) 226 8.4.1 Addition of Alcohols to Allenes 226 8.4.2 Cyclization of Allenyl and Propargyl Ketones 227 8.4.3 Addition of Alcohols to Alkenes 230 References 234 9 Gold-Catalyzed Aldol and Related Reactions 237 Christoph Hubbert and A.
Load more

Recommended publications
  • Synthesis by Successive Ionic Layer Deposition (SILD) Methodology and Characterization of Gold Nanoclusters on the Surface of Tin and Indium Oxide Films
    DOI 10.1515/pac-2013-1102 Pure Appl. Chem. 2014; 86(5): 801–817 Conference paper Ghenadii Korotcenkov, Larisa B. Gulina*, Beongki Cho*, Vladimir Brinzari and Valery P. Tolstoy Synthesis by successive ionic layer deposition (SILD) methodology and characterization of gold nanoclusters on the surface of tin and indium oxide films Abstract: The ability of successive ionic layer deposition (SILD) technology to synthesize gold clusters on the surface of tin(IV) oxide and indium(III) oxide films is discussed. It was shown that during the process, concen- tration of active sites that are capable of absorbing gold ions, and the size of the gold particles thus formed, may be controlled by both concentration of the solutions used and the number of SILD cycles. Thus, SILD methodol- ogy, employing separate and multiple stages of adsorption and reduction of adsorbed species, has considerable potential for customizing the properties of the deposited metal nanoparticles. In particular, it is shown that during the deposition of gold nanoparticles on the surface of tin(IV) oxide and indium(III) oxide films by SILD methodology, conditions can be realized under which the size of gold nanoclusters may be controllably varied between 1–3 nm and 50 nm. A model is proposed for the formation of gold clusters during the SILD process. Keywords: absorption; Au nanoparticles; characterization; chemical synthesis; deposition; gold; In2O3; NMS- IX; particles; scanning electron microscopy (SEM); SnO2; successive ionic layer deposition (SILD); surface modification. *Corresponding authors: Larisa B. Gulina, Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russia, e-mail: [email protected]; and Beongki Cho, Gwangju Institute of Science and Technology, Department of Material Science and Engineering, Gwangju, Korea, e-mail: [email protected] Valery P.
    [Show full text]
  • UC Riverside UC Riverside Electronic Theses and Dissertations
    UC Riverside UC Riverside Electronic Theses and Dissertations Title Developing Modular Syntheses of Diverse Nitrogen Heterocycle-Based Compounds for Metal Complexes, Catalysis, and Therapeutics Permalink https://escholarship.org/uc/item/9hz352x2 Author Sterling, Michael David Elliott Publication Date 2019 Peer reviewed|Thesis/dissertation eScholarship.org Powered by the California Digital Library University of California UNIVERSITY OF CALIFORNIA RIVERSIDE Developing Modular Syntheses of Diverse Nitrogen Heterocycle-Based Compounds for Metal Complexes, Catalysis, and Therapeutics A Dissertation submitted in partial satisfaction of the requirements for the degree of Doctor of Philosophy in Chemistry by Michael David Elliott Sterling March 2019 Dissertation Committee: Dr. Catharine H. Larsen, Chairperson Dr. Christopher Switzer Dr. Chia-en Chang Copyright by Michael David Elliott Sterling 2019 The Dissertation of Michael David Elliott Sterling is approved: Committee Chairperson University of California, Riverside DEDICATION To all the people in my life who, without their support, guidance, and love, I would not be where I am today. This section and the following are dedicated to you. First, to my advisor Catharine: thank you for seeing the potential in me, even when I didn’t see it myself. I entered this journey feeling thoroughly unconvinced I could handle it, but your unwavering support and guidance is the reason I am here today. I know it hasn’t been an easy five years by any means, but I wouldn’t rather have taken this trip with anyone but you. I will look back on my time at UCR with pride, as I was fortunate to work for such an amazing chemist, person, and friend.
    [Show full text]
  • Compounds and Catalysts
    Precious Metal Compounds and Catalysts Ag Pt Silver Platinum Os Ru Osmium Ruthenium Pd Palladium Ir Iridium INCLUDING: • Compounds and Homogeneous Catalysts • Supported & Unsupported Heterogeneous Catalysts • Fuel Cell Grade Products • FibreCat™ Anchored Homogeneous Catalysts • Precious Metal Scavenger Systems www.alfa.com Where Science Meets Service Precious Metal Compounds and Table of Contents Catalysts from Alfa Aesar When you order Johnson Matthey precious metal About Us _____________________________________________________________________________ II chemicals or catalyst products from Alfa Aesar, you Specialty & Bulk Products _____________________________________________________________ III can be assured of Johnson Matthey quality and service How to Order/General Information ____________________________________________________IV through all stages of your project. Alfa Aesar carries a full Abbreviations and Codes _____________________________________________________________ 1 Introduction to Catalysis and Catalysts ________________________________________________ 3 range of Johnson Matthey catalysts in stock in smaller catalog pack sizes and semi-bulk quantities for immediate Precious Metal Compounds and Homogeneous Catalysts ____________________________ 19 shipment. Our worldwide plants have the stock and Asymmetric Hydrogenation Ligand/Catalyst Kit __________________________________________________ 57 Advanced Coupling Kit _________________________________________________________________________ 59 manufacturing capability to
    [Show full text]
  • Safety Data Sheet 29 CFR 1910.1200
    CMI Product #2007 Issued 12/15/15 Product# 2007 Safety Data Sheet 29 CFR 1910.1200 Section 1: Company and Product Identification Product Name: Sodium Tetrachloroaurate (III) hydrate Product Code: 2007 Company: Colonial Metals, Inc. Building 20 505 Blue Ball Road Elkton, MD 21921 United States Company Contact: EHS Director www.colonialmetals.com Telephone Number: 410-398-7200 FAX Number: 410-398-2918 E-Mail : [email protected] Web Site: www.colonialmetals.com Emergency Response: Supplier Emergency Contacts & Phone Number Chemtrec: 800-424-9300 World Wide - Call COLLECT to U.S: 703-527-3887 Section 2: Hazards Identification GHS07 BLANK BLANK BLANK Hazard Pictograms: Signal Word: Warning Hazard Category: Acute tox, dermal Cat 4 Serious eye damage/eye irritation Cat 3 Aspiration hazard Cat 2 Acute tox, oral Cat 4 Hazard Statements: H312: Harmful in contact with skin H320: Causes eye irritation H305: May be harmful if swallowed and enters airways H302: Harmful if swallowed P260: Do not breathe dust/fume/gas/mist/vapors/spray P303+361+353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated P305+351+338: IF IN EYES: Rinse cautiously with water for several minutes. Remove P301+330+331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting P405: Store locked up P501: Dispose of contents/container in accordance with local/regional/national/international rules. Hazards not To the best of our knowledge the chemical, physical, and toxicological effects of this otherwise classified: compound have not been thoroughly investigated. Section 3: Composition / Information on Ingredients Hazardous substance (name) Hazard Category CAS# Weight % Sodium Tetrachloroaurate (III) hydrate Irritant 13874-02-7 98 - 100 Chemical Family: Group 1B Metal Salt Chemical Formula: NaAuCl4.2H20 Synonyms: Gold chloride, Sodium salt hydrate US-SDS 1 of 4 4/11/2016 CMI Product #2007 Issued 12/15/15 Section 4: First Aid Measures General Info: Ensure proper ventilation.
    [Show full text]
  • Chrysotype: Photography in Nanoparticle Gold
    Chrysotype: Introduction Gold has always played a role in photography as the ultimate Photography in means of stabilizing and protecting the silver image, the universal commercial medium. Since the dawn of the art- science of photography around 1840, a gold complex salt Nanoparticle Gold (1), sodium bisthiosulphatoaurate(I) was used to ‘gild’ the images of daguerreotypes by depositing gold metal on the surface of the silver: Mike Ware 3- 3- 20 Bath Road, Buxton, SK17 6HH, UK Ag + [Au(S2O3)2] Au + [Ag(S2O3)2] e-mail: [email protected] In 1847, this was also recommended for the stabilization of silver photographic prints on paper. In this way, vulnerable Abstract silver images were protected from the sulphiding action of the The printing of photographs in pure gold, rather than polluted industrial atmospheres of the Victorian era, which the ubiquitous medium of silver, was first achieved in otherwise caused them to tarnish or fade. From 1855 onwards, 1842 by Sir John Herschel, but his innovative the gold toning of silver salted paper and albumen prints ‘chrysotype’ process was soon consigned to obscurity, became standard practice, such that the British Government owing to its expense and uncertain chemistry. In the Photographer in India, Linnaeus Tripe, was moved to advise his 1980s some modern coordination chemistry of gold colleagues “Not to spare the sovereigns!” (2). This important was applied to overcome the inherent problems, application of gold in photography has previously been enabling an economic, controllable gold-printing reviewed in the Gold Bulletin by P Ellis (3). process of high quality, which offers unique benefits But if gold is such a stable image substance, why not by- for specialised artistic and archival photographic pass the use of reactive silver altogether, and make purposes.
    [Show full text]
  • Precious Metal Compounds and Catalysts
    Precious Metal Compounds and Catalysts Ag Pt Silver Platinum Os Ru Osmium Ruthenium Pd Palladium Ir Iridium INCLUDING: • Compounds and Homogeneous Catalysts • Supported & Unsupported Heterogeneous Catalysts • Fuel Cell Grade Products • FibreCat™ Anchored Homogeneous Catalysts • Precious Metal Scavenger Systems www.alfa.com Where Science Meets Service Precious Metal Compounds and Table of Contents Catalysts from Alfa Aesar When you order Johnson Matthey precious metal About Us _____________________________________________________________________________ II chemicals or catalyst products from Alfa Aesar, you Specialty & Bulk Products _____________________________________________________________ III can be assured of Johnson Matthey quality and service How to Order/General Information ____________________________________________________IV through all stages of your project. Alfa Aesar carries a full Abbreviations and Codes _____________________________________________________________ 1 Introduction to Catalysis and Catalysts ________________________________________________ 3 range of Johnson Matthey catalysts in stock in smaller catalog pack sizes and semi-bulk quantities for immediate Precious Metal Compounds and Homogeneous Catalysts ____________________________ 19 shipment. Our worldwide plants have the stock and Asymmetric Hydrogenation Ligand/Catalyst Kit __________________________________________________ 57 Advanced Coupling Kit _________________________________________________________________________ 59 manufacturing capability to
    [Show full text]
  • In Situ Study of Au/C Catalysts for the Hydrochlorination of Acetylene
    In situ Study of Au/C Catalysts for the Hydrochlorination of Acetylene Thesis submitted in accordance with the requirements of Cardiff University for the degree of doctor of philosophy by Grazia Malta School of Chemistry Cardiff University 2018 Supervisor Prof. Graham Hutchings DECLARATION This work has not been submitted in substance for any other degree or award at this or any other university or place of learning, nor is being submitted concurrently in candidature for any degree or other award. Signed ……………………………………………………… (candidate) Date ………………….…………….……… STATEMENT 1 This thesis is being submitted in partial fulfillment of the requirements for the degree of ………(insert MCh, MD, MPhil, PhD etc, as appropriate) Signed ………………………………………….…………… (candidate) Date …………………………….…………… STATEMENT 2 This thesis is the result of my own independent work/investigation, except where otherwise stated, and the thesis has not been edited by a third party beyond what is permitted by Cardiff University’s Policy on the Use of Third Party Editors by Research Degree Students. Other sources are acknowledged by explicit references. The views expressed are my own. Signed ……………………………………….……….…… (candidate) Date …………………….………………… STATEMENT 3 I hereby give consent for my thesis, if accepted, to be available online in the University’s Open Access repository and for inter-library loan, and for the title and summary to be made available to outside organisations. Signed ……………………………………………..…..….. (candidate) Date ………………………………………… STATEMENT 4: PREVIOUSLY APPROVED BAR ON ACCESS I hereby give consent for my thesis, if accepted, to be available online in the University’s Open Access repository and for inter-library loans after expiry of a bar on access previously approved by the Academic Standards & Quality Committee.
    [Show full text]
  • Coupling Reactions
    Routes to organogold compounds and gold catalysed A3-coupling reactions A thesis submitted to the University of Manchester for the degree of Doctor of Philosophy in the Faculty of Engineering and Physical Sciences. 2013 Gregory Arthur Price School of Chemistry Contents Abbreviations ...................................................................................................................................... 7 Abstract ............................................................................................................................................. 11 Declaration ........................................................................................................................................ 12 Copyright .......................................................................................................................................... 13 Acknowledgments ............................................................................................................................. 14 1 The Chemistry of Gold ............................................................................................................. 15 1.1 Introduction ....................................................................................................................... 15 1.2 Oxidation states of gold .................................................................................................... 16 1.2.1 Gold(I) complexes..................................................................................................... 16
    [Show full text]
  • L-G-0009995667-0020105508.Pdf
    Handbook of Reagents for Organic Synthesis Reagents for Heteroarene Synthesis OTHER TITLES IN THIS COLLECTION Reagents for Organocatalysis Edited by Tomislav Rovis ISBN 978 1 119 06100 7 Reagents for Heteroarene Functionalization Edited by Andre´ Charette ISBN 978 1 118 72659 4 Catalytic Oxidation Reagents Edited by Philip L. Fuchs ISBN 978 1 119 95327 2 Reagents for Silicon-Mediated Organic Synthesis Edited by Philip L. Fuchs ISBN 978 0 470 71023 4 Sulfur-Containing Reagents Edited by Leo A. Paquette ISBN 978 0 470 74872 5 Reagents for Radical and Radical Ion Chemistry Edited by David Crich ISBN 978 0 470 06536 5 Catalyst Components for Coupling Reactions Edited by Gary A. Molander ISBN 978 0 470 51811 3 Fluorine-Containing Reagents Edited by Leo A. Paquette ISBN 978 0 470 02177 4 Reagents for Direct Functionalization for C–H Bonds Edited by Philip L. Fuchs ISBN 0 470 01022 3 Reagents for Glycoside, Nucleotide, and Peptide Synthesis Edited by David Crich ISBN 0 470 02304 X Reagents for High-Throughput Solid-Phase and Solution-Phase Organic Synthesis Edited by Peter Wipf ISBN 0 470 86298 X Chiral Reagents for Asymmetric Synthesis Edited by Leo A. Paquette ISBN 0 470 85625 4 Activating Agents and Protecting Groups Edited by Anthony J. Pearson and William R. Roush ISBN 0 471 97927 9 Acidic and Basic Reagents Edited by Hans J. Reich and James H. Rigby ISBN 0 471 97925 2 Oxidizing and Reducing Agents Edited by Steven D. Burke and Rick L. Danheiser ISBN 0 471 97926 0 Reagents, Auxiliaries, and Catalysts for C–C Bond Formation Edited by Robert M.
    [Show full text]
  • Pyrandione, Thiopyrandione and Cyclohexanetrione Compounds Having Herbicidal Properties
    (19) TZZ ¥¥¥_T (11) EP 2 527 333 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 28.11.2012 Bulletin 2012/48 C07D 263/32 (2006.01) C07D 277/24 (2006.01) C07D 293/06 (2006.01) C07D 333/10 (2006.01) (2006.01) (2006.01) (21) Application number: 12170624.6 C07D 403/04 C07D 409/04 C07D 417/04 (2006.01) A01N 43/76 (2006.01) (2006.01) (22) Date of filing: 26.06.2008 A01N 43/78 (84) Designated Contracting States: (72) Inventors: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR • Jeanmart, Stephane André Marie HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT 4332 Stein (CH) RO SE SI SK TR • Mathews, Christopher John Bracknell, Berkshire RG42 6EY (GB) (30) Priority: 28.06.2007 GB 0712653 • Taylor, John Benjamin Bracknell, Berkshire RG42 6EY (GB) (62) Document number(s) of the earlier application(s) in • Smith, Stephen Christopher accordance with Art. 76 EPC: Bracknell, Berkshire RG42 6EY (GB) 08784557.4 / 2 173 727 • Phadte, Mangala 403110 Goa (IN) (71) Applicant: Syngenta Limited Guildford Remarks: Surrey GU2 7YH (GB) This application was filed on 01-06-2012 as a divisional application to the application mentioned under INID code 62. (54) Pyrandione, thiopyrandione and cyclohexanetrione compounds having herbicidal properties 5 (57) Pyrandione, thiopyrandione and cyclohexane- wherein Y is O, C=O, S(O)m or S(O)nNR ; provided that trione compounds having herbicidal properties have when Y is C=O, R3 and R4 are different from H when been found.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 8,530,667 B2 Jeanmart Et Al
    USOO853.0667B2 (12) United States Patent (10) Patent No.: US 8,530,667 B2 Jeanmart et al. (45) Date of Patent: Sep. 10, 2013 (54) HERBICIDES (52) U.S. Cl. USPC .......... 548/100: 548/204:546/287.7: 549/60; (75) Inventors: Stephane André Marie Jeanmart, 549/459; 549/78; 54.4/318 Bracknell (GB); John Benjamin Taylor, (58) Field of Classification Search Bracknell (GB); Melloney Tyte, None Bracknell (GB); Christopher John See application file for complete search history. Mathews, Bracknell (GB); Stephen Christopher Smith, Bracknell (GB) (56) References Cited (73) Assignee: Syenta Limited, Guildford, Surrey U.S. PATENT DOCUMENTS (GB) 2005, 0164883 A1 7/2005 Maetzke (*) Notice: Subject to any disclaimer, the term of this 58-385 A. 585 May patent is extended or adjusted under 35 2012/0094832 A1 4/2012 Tyte et al. U.S.C. 154(b) by 116 days. 2012/0142529 A1 6/2012 Tyte et al. (21) Appl. No.: 12/675,975 FOREIGN PATENT DOCUMENTS WO 96.03366 2, 1996 (22) PCT Filed:1-1. Sep. 1, 2008 WO O17477O9948869 10,9, 20011999 (86). PCT No.: PCT/EP2008/007 132 W. 3352 1358. S371 (c)(1), Primary Examiner — Nyeemah A Grazier (2), (4) Date: Jun. 15, 2010 (74) Attorney, Agent, or Firm — R. Kody Jones (87) PCT Pub. No.: WO2009/030450 (57) ABSTRACT PCT Pub. Date: Mar. 12, 2009 Compounds of formula (I) wherein the substituents are as (65) Prior Publication Data defined in claim 1, are suitable for use as herbicides. US 2010/O29814.0 A1 Nov. 25, 2010 (I) (30) Foreign Application Priority Data Sep.
    [Show full text]
  • May 8, 1973 D
    May 8, 1973 D. BROWN ETAL 3,732,094 PROCESS FOR PREPARING ELEMENTAL MERCURY Filed June 29, 1970 8 Sheets-Sheet 1 BY ???? ATTORNEYS May 8, 1973 D. BROWN ETA 3,732,094 PROCESS FOR PREPARING ELEMENTAL MERCURY Filled June 29, 1970 8 Sheets-Sheet 4 9NIHOVET–139w1s INVENTORS ALTON R. CARLSON DUANE BROWN BY ATTORNEYS May 8, 1973 D. BROWN ET AL 3,732,094 PROCESS FOR PREPARING ELEMENTAL MERCURY Filed June 29, 1970 8 Sheets-Sheet : NOI.Ld8OSOV/ ? 9NITLLES NOIIVOIHIHnd–z39WLS 8º INVENTORS ALTON R. CARLSON DUANE BROWN BY ATTORNEYS May 8, 1973 D. BROWN ETAL 3,732,094 PROCESS FOR PREPARING ELEMENTAL MERCURY Filed June 29, 1970 09.2° AMJBAOOBHTVLEWSTOIOB}}dTVNOI.LdO 239\/]LS-JOdB.LS DUANE BROWN li?BY A TORNEYS May 8, 1973 D. EROVVN ET AL 3,732,094 PROCESS FOR PREPARING ELEMENTAL MERCURY Filed June 29, 1970 8 Sheets-Sheet , 31.ooosx9NINIVILNO? QOHLEWGEMJH3-||38d:NO|100038-239WLS -OL1STATOV; ATTORNEYS May 8, 1973 D. BROWN ET AL 3,732,094 PROCESS FOR PREPARING ELEMENTAL MERCURY Filed June 29, l970 8 Sheets-Sheet 7 OBVOS#C) BLATOHLOBT3LNBdS AHEAOOBHLN30V3HNOILOnQ38-v39\/1S E9NOCHSuS OILNO|LOTAGE}} E9NOdSUS INVENTORS A TON R. CARLSON DUANE BROWN ATTORNEYS May 8, 1973 D. BROWN ET AL 3,732,094 PROCESS FOR PREPARING ELEMENTAL MERCURY Filed June 29, 1970 ?? 8 Sheets-Sheet 3 98 dELSNOILOTIC]38 NOllwg3N3938LN39v38NOILOnQ38–G39WLS INVENTORS ATON. R. CARLSON DUANE BROWN BY ATTORNEYS 3,732,094 United States Patent Office Patented May 8, 1973 2 Similarly, according to still another aspect of the inven 3,732,094 tion, if precious metals such as gold compounds are pres PROCESS FOR PREPARNG ELEMENTAL ent, they are selectively separated from the pregnant mer MERCURY Duane Brown, 104 E.
    [Show full text]