Modern Synthetic Methods – serie
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Modern Synthetic Methods 1986
Conference Papers of the International Seminar on Modern Synthetic Methods 1986, Interlaken, April 17th/18th 1986
Häftad, Engelska, 1986
1 075 kr
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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 .,.
1 073 kr
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This paperback is the conference documentation of the fifth Seminar on MODERN SYNTHETIC METHODS 1989. It is the aim of these triennial Interlaken-Seminars to provide a proper, concine and "ready for use" acceos to important and rapidly developing areas of synthetic organic chemistry. Usefu.l synthetic methods have to combine economic and ecological aspects. The search for such methods is a continuous scientific challenge. It implies a solid knowledge a~d updated information on current prospects in biochemistry, organic as well as inorganic chemiotry. The main themes of the 1989-Seminar are "Biotransformations in Organic Synthesis", "Enantioselective Catalyois with Metal Complexes" and "Aluminosilicates in Organic Synthesis". These topics have been chosen, since they reflect the enormous progress in experience and understanding of catalysis in organic syntheGis. This book if' the compilation of the contributions provided by the lecturers of the Seminar. The reviews are written by leading experts and describe not only the basic concepts, their application in oynthesis but also contain representative experimental procedures. The purpose of this volume is twofold. It should aid participants and students in followi~g the lectures. The main reason, however, is to serve ao an updated guide for chemists interested in catalyois applied to organic synthesis.