Modern Synthetic Methods 1986: Conference Papers of the International Seminar on Modern Synthetic Methods 1986, Interlaken, April 17th/18th 1986

Author:   H.C. Brown ,  R. Scheffold ,  M. Demuth ,  G. Helmchen
Publisher:   Springer-Verlag Berlin and Heidelberg GmbH & Co. KG
Edition:   Softcover reprint of the original 1st ed. 1986
Volume:   4
ISBN:  

9783540165262


Pages:   356
Publication Date:   01 April 1986
Format:   Paperback
Availability:   Out of stock   Availability explained
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Modern Synthetic Methods 1986: Conference Papers of the International Seminar on Modern Synthetic Methods 1986, Interlaken, April 17th/18th 1986


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Overview

In the tricyclooctanone approach to polyquinane syntheses[ll the photochemical rearrangement of bicyclo[2.2.2]octenone, 1a 2a,[2J has been the initial key reaction providing tricyclo- 2 [3.3.0.0 ' S]octan-3-one as a chiral building block.[3-SJ This reaction - an oxadi-n-methane (ODPM) process - and the 1,3-acyl shift (AS) forming the cyclobutanone 3 are quite generally the characteristic re- arrangement paths undergone by ~,~-unsaturated ketones (~,~-UKs) upon triplet sensitization and direct excitation with ultraviolet light, respectively. R' R' hv hv R~O ~ ~ (sens) WO ~ R ONR R 1a-c 2a-c 3a-c a R=R'=H b R = CH , R'= H 3 c R = R'= CH 3 As a polyvalent building block, the enantiomers of which are readily accessible from cheap bulk chemicals such as benzene and its derivatives, the parent system 1a and three younger generations of its class (Sections 3.1. - 3.4.) have no equal among synthetically useful photochemical rearrangements. 2. THE PHOTOCHEMISTRY OF ~,~-UNSATURATED KETONES The literature dealing with the spectroscopy and photo- chemistry of ~,~-UKs has been exhaustively and critically reviewed around 1975 by Dauben et al.[6l and Houk,[7J and in 1980 by Schuster.[ SlI1 The 1,3-AS was first observed on direct excitation of 1) For more recent papers on i3,~-UK photochemistry see [9-24]. 64 ~ R' hv ~o hv .,.

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Author:   H.C. Brown ,  R. Scheffold ,  M. Demuth ,  G. Helmchen
Publisher:   Springer-Verlag Berlin and Heidelberg GmbH & Co. KG
Imprint:   Springer-Verlag Berlin and Heidelberg GmbH & Co. K
Edition:   Softcover reprint of the original 1st ed. 1986
Volume:   4
Dimensions:   Width: 14.80cm , Height: 1.90cm , Length: 21.00cm
Weight:   0.485kg
ISBN:  

9783540165262


ISBN 10:   3540165266
Pages:   356
Publication Date:   01 April 1986
Audience:   College/higher education ,  Professional and scholarly ,  Undergraduate ,  Postgraduate, Research & Scholarly
Format:   Paperback
Publisher's Status:   Active
Availability:   Out of stock   Availability explained
The supplier is temporarily out of stock of this item. It will be ordered for you on backorder and shipped when it becomes available.

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