CHEMISTRY OF SILYL THIOKETONES .8. PHOTOINDUCED CYCLOADDITIONS OF SILYL THIOKETONES WITH OLEFINS

Authors
BONINI BF FRANCHINI MC FOCHI M MAZZANTI G RICCI A ZANI P ZWANENBURG B
Citation
Bf. Bonini et al., CHEMISTRY OF SILYL THIOKETONES .8. PHOTOINDUCED CYCLOADDITIONS OF SILYL THIOKETONES WITH OLEFINS, Journal of the Chemical Society. Perkin transactions. I, (16), 1995, pp. 2039-2044
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
16
Year of publication
1995
Pages
2039 - 2044
Database
ISI
SICI code
0300-922X(1995):16<2039:COST.P>2.0.ZU;2-P
Abstract
Photo-induced cycloadditions of phenyl triphenylsilyl thioketone 1 wit h electron-poor olefins (acrylonitrile, methyl acrylate and cis- and t rans-1,2-dichloroethene) gave silyl thietanes in a regio- and highly s tereoselective manner. In contrast, reaction with vinyl ethers gave th ietanes without any regio- or stereo-control. Reaction with alpha-meth ylstyrene and 2,3-dimethylbut-2-ene gave open chain products. Desilyla tion of silyl thietanes occurs with prevalent inversion of configurati on at the carbon bearing the silicon group.