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Showing 1 - 25 of
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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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Flame (Paperback)
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R356
Discovery Miles 3 560
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Reno (Paperback)
H. C. Brown
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R327
Discovery Miles 3 270
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Nox (Paperback)
H. C. Brown
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R270
Discovery Miles 2 700
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Roar (Paperback)
H. C. Brown
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R261
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Pride (Paperback)
H. C. Brown
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R293
Discovery Miles 2 930
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