General and Synthetic Methods Volume 7 / A Specialist Periodical Report l*h, General and Synthetic Methods Volume 7 A Review of the Literature Published during 1982 Senior Reporter G. Pattenden, Department of Chemistry, University of Nottingham Reporters R. C. Brown, Fisons PAC., Loughborough, Leicestersbire K. Cooper, Pfizer Central Research, Sandwich S. C. Eyley, Fisons p.l.c., Loughborough, Leicestershire P. F. Gordon, 1.C.I. Organics Division, Manchester D . M. Hollinshead, Imperial College, London P. R. Jenkins, University of Leicester R. C. F. Jones, University of Nottingham G . Kneen, Wellcome Research Laboratories, Beckenham, Kent T. V. Lee, Brunel University, Uxbridge S . V. Ley, Imperial College, London A. J. Nelson, I.C.1. Organics Division, Manchester G . M Robertson, University of Nottingham The Royal Society of Chemistry Burlington House, London W I V OBN LSBN 0-85186-884-3 ISSN 0141-2140 Copyright 0 1985 The Royal Society of Chemistry All Rights Reserved No part of this book may be reproduced or transmitted in any form or by any means-graphic, electronic, including photocopying, recording, taping or information storage and retrieval systems-without written permission from the Royal Society of Chemistry Typeset by Bath Typesetting Ltd., Bath, and printed by J. W. Arrowsmith Ltd., Bristol, England Made in Great Britain Introduction This Report on General and Synthetic Methods, which covers the literature from January to December 1982, is similar in scope and format to the previous volumes in the series. Without question, one of the major achievements in synthesis to be published during 1982 was the synthesis of dodecahedrane by Paquette and his co-workers (J. Am. Chem. SOC., 1982, 104, 4503). This molecule (€9,regarded by many scientists as the ‘Mount Everest of Alicyclic Chemistry’ is the structurally most complex, symmetric member of the C,H, convex polyhedra. Paquette’s synthesis of dodecahedrane, which is briefly summarized in the Scheme (overleaf), features the homo-Norrish photochemical bond-formation of a ketone carbonyl carbon to a neighbouring carbon atom, e.g. (1) --+ (2), (3) + (4), and (5) -+ (6), to ‘stitch’ together many of the cyclopentane rings in the molecule, with the final ring being closed by dehydrogenation of (7). Dodecahedrane is a crystalline solid which does not melt below 450 OC, As anticipated, the molecule shows sharp singlets in both its lH and 13C n.m.r. spectra, at 6 3.38 and 6 66.93 p.p.m. respectively. The synthesis of dodecahedrane is an achievement of great theoretical and potential practical importance, and it is fitting that for this contribution, and for many other outstanding contributions to organic synthesis,Paquette has been awarded the ACS 1984 National Award for Creative Work in Synthetic Organic Chemistry. October I983 G . PATTENDEN Introduction vi Me0 PhOH,C - - c1 ( i ) 9 steps OMe To Li,NH, ( i i ) PhOCHzCl HO Me0 @ /
[email protected] hV f-- 4 steps f-- HO H KOH 4 Pd/C 250 "C 0 Contents Chapter 1 Saturated and Unsaturated Hydrocarbons By K. Cooper 1 1 Saturated Hydr