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Xarox University Microfilms INFORMATION TO USERS Thil material was produced from a microfilm copy of the original documant. While the moat advanced technological meant to photograph and reproduce this documant have been used, the quality is heavily dependant upon the quality of the original submitted. The following explanation o f techniques is provided to help you understand markings or patterns which m ay appear on this reproduction. 1. The sign or "target" for pages apparently lacking from the document photographed is "Misting Page(s)". If it was possible to obtain the misting page(s) or section, th a y era spliced into the film along with adjacent pages. This may have necessitated cutting thru an image and duplicating adjacent pagae to insure you complete continuity. 2. Whan an image on th e 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 causa a blurred image. You will find a good image of the pnga in the adjacent frame. 3. Whan a map, drawing or chart, etc., was part of the material being photographed the photographer followed a definite method in "sectioning" the material. It ie customary to begin photoing at the upper left hand comer of a large sheet and to continue photoing from left to right in equal sections with a small overlap. If necessary, sectioning is continued again — beginning below the first row end continuing on until complete. 4. The majority of users indicate that the textual content is of greatest value, however, a somewhat higher quality reproduction could be made from "photographs" if essential to the understanding of the dissertation. Silver prints of "photographs" may be ordered at additional charge by writing the Order Department, giving the catalog number, tide, author and specific pages you w ish reproduced. 5. PLEASE NOTE: Some pages may have indistinct print. Filmed as received. Xarox University Microfilms 300 North ZMbRMd Ann Arbor, Michigan 4S100 PRESS, J e ff e r y B ruce, 191*7- SYNTHESIS AND CHEMISTRY OF BICYCL0[4.2 .2]DECA- 2,H,9-TRIEN-7-ONE AND BICYCL0[«+.2.2;)DECA- 2,h,9-TRIEN-7-YL INTERMEDIATES. The Ohio State University, Ph.D., 1973 Chemistry, organic University Microfilms. A XEROX C o m pany # Ann Arbor. Michigan j THIS DISSERTATION HAS BEEN MICROFILMED EXACTLY AS RECEIVED. SYNTHESIS AND CHEMISTRY OP BICYCL0[4.2.2]DECA-2,lf;9-®IEN-7-0NE AND BICYCLOL^.2.2'JDECA-2A;9-TRIEN-7-YL INTERMEDIATES DISSERTATION Presented In Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio S ta te U niversity By Jeffery Bruce Press, B.S. # * * * * The Ohio S ta te U niversity 1973 Reading Conmittee; Approved hy Dr. Harold Shecbter Dr. Paul Gassman Dr. Robert Ouellette Adviser Department of Chemistry DEDICATION To my parents 11 ACKNOWLEDGMENT The author is grateful to Dr. Harold Shechter for suggestion of this problem, for his ever-present enthusiasm and Imaginative guidance and for his aid in preparing this manuscript. Dr. Shechter's wit, imagination, and knowledge provided stimulation and encouragement during the course of study. The author is indebted to Messrs. Gary Blrriberg and J. Michael Geckle and Dr. Paul Gassman for enlightening discussions concerning exper­ imental results. He is further indebted to Mr. Geckle for both measure­ ment and Interpretation of nmr data which was essential for completion of this work and to Miss Carol Rose for her skill and patience in typing and illustrating the final manuscript. The author also wishes to acknow­ ledge interesting discussions of both chemical and non-chemical nature with Messrs. Blrnberg, Geckle, Roger Drewes, and Gordon Gruetzmacher at local pubs in Columbus. The author must express deep appreciation to Fhilllpus Aureolus Theophrastus Bombastus von Hohenhelm who provides the eternal light to alchemists everywhere and lastly to his wife, Debbie, whose many lonesome nights allowed completion of much of thiB work. i l l VITA May 2h, 1 9 k 7.................................................. Born - Rochester, New York 1 9 ^ 9 ................................................................... B.S. - BuckneU University, Lewishurg, Pennsylvania 1 96 9 -1 9 7 3 ........................................................ Teaching Assistant, Department of Chemistry, The Ohio State Univer­ sity, Colunibus, Ohio 1973 . ............................................................... Research Associate, Department of Chemistry, The Ohio State Univer­ sity, Columbus, Ohio PUBLICATIONS 'The Chemistry of Bicyclo[^.2.11nona-2,^,7-trien-9-one, Bicyclo(.U.2.1]- nona-2,4,7-trien-9-yl Intermediates and Their Derivatives," T. A, Antkowiak, D. C. Sanders, G. B. Trimitsis, J. B. Press, and H. S hechter, J . Amer. Chem. S o c., 9hj 3366 (1972). “Facile Synthesis of Bicyclo[4.2.21deca-2,4,7>9-Tetraenes," J. B. Press and H. Shechter, Tet. Letters, 2677 (1972). iv TABLE OF CONTENTS Page DEDICATION............................................................................................................................ 11 ACKNOWLEDGMENTS ................................................................................................................. I l l VITA.......................................................................................................................................... lv LIST OF TABLES.................................................................................................................... x STATEMENT OF PROBLEM....................................................................................................... I HISTORICAL................................................ 2 RESULTS AND DISCUSSION................................................................................................... IT SUMMARY.................................................................................................................................... 77 EXPERIMENTAL...................................................................... 80 . General Procedures and Techniques ............................................................... 60 Preparation of Biqyclo[4.2.1]nona-2,li,7-trien-9-one ....................... 8 l Reaction of Bieyclo[U.2.1]nona-2,lf,7-trien-9-one with Diazomethane ......................................................................................................... 6 Reaction of Bicyclo[^.2.2]deca-2,lt-,9-trien-7-one (l) with Semicarhazlde Hydrochloride ....................................................................... 82 Preparative Isolation of Bicyclo[lj-.2.23deca-2,U,9-trien- 7 -one ( l ) .............................................. 83 Reaction of Bicyclo£h.2.2]deca-2,lf,9-trien-7-one (l) with 2,l*-Dinitrophenylhydrazine ............................................7*. ........................ 8^ Reaction of Bicydo[J|.2.2]deca-2,if,9,"trien-7-one (l) with Hydroxylamine H y d ro c h lo rid e ........................................................................ 8*f Catalytic Hydrogenation of Bicyclo[i|. 2.2]deca-2,^,9-trien- 7 -o n e ( l ) ................................................................................................................ 83 V Page Reaction of Bicyclo[4.2.2]decan-7-one (4) with 2,lf-Dinitro- phenylhydrazine ........................................... 7 . .......................... 65 Reaction of Bicyclo[l+.2.2]decan-7-one (U) with Semlcarbazide Hydrochloride ................................................................................................... 66 Catalytic Hydrogenation of Bicyclo[U.2. l]nona-2,U,7-trien- 9 - o n e .................................. ............................................-.................................• . 86 Reaction of Bicyclo[U.2.1]nonan-9-one ( 6) with Diazomethane ... 87 Base-Catalyzed Mono- and Dideuteratlon of Blcyclo[U.2.2Jdeoa- 2 ,U ,9 - tr ie n - 7-one ( l ) ......................................................... 87 Reaction of Bicydo[U.2.2]deca-2,J+,9-trien-7-one (l) with * * Potassium t-Butoxlde and Deuterium O xide ............. 7 . ...................... 88 Reaction of Bicyclo[U.2.2]deca-2,4,9-trlen-7“One (l) with Potassium t-B u to x id e and Water in Dim ethylform aml'de........ 88 Reaction of Bicyclo[^.2.2]deea-2,4,9-trien-7-one (l) with ToBylhydrazlde .....................................................................7 . ...................... 89 Reaction of Bicyclo[^.2.2]deca-2,4,9**trien-7-one (l) with Benzenesulfonylhydrazide ............................................... 7 . ...................... 89 Reaction of Bicyclo[4.2.2]deca-2,4,9-trien-7-one Tosylhydra- zone (12) with M ethylllthium ................................................................... 90 Reaction of Bicydo[4.2.2]deca-2,4,9-trien-7-one (l) with Isopropenyl A cetate .......................................................... 7 . ...................... 91 Reaction of Bicyclo[U.2.2]deca-2,l*,9-trien-7-one (l) with Potassium t-Butoxide and Acetyl Chloride in Glyme ...................... 91 Reaction of 7-Acetoxybicyclo[if.2.2]deca-2,^,7j9-tetraene ( 15 ) with 3N Hydrochloric A cid ......................................................................... 92 Reaction of B icy do [4.2.2]deca-2, U, 9-trien-7-one (l) with Pyrrolidine ............................................................................7 . ...................... 92 Reaction of 7-Pyrrolidinobicyclo[l;.2.2]deca-2,U,7>9-tetraene (1 6) with 3N Hydrochloric A cid ............................................................. 95 Reaction of Bicyclo[4.2.2]deca-2,U,9-trien-7-one
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