Photochemical Formation and Reactivities of Substituted Oxathiiranes in Low??Temperature Argon Matrices

HP Reisenauer, G Mloston, J Romanski…

Index: Reisenauer, Hans Peter; Mloston, Grzegorz; Romanski, Jaroslaw; Schreiner, Peter R. European Journal of Organic Chemistry, 2011 , # 31 p. 6269 - 6275

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Abstract

Abstract Thiocarbonyl S-oxides (sulfines) derived from aliphatic and cycloaliphatic thioketones were irradiated in argon matrices at 10 K, and the resulting oxathiiranes were identified by comparison of computed and experimental IR spectra. Upon photolysis at 10 K, depending on the substitution pattern, the oxathiiranes underwent either H-shift reactions or regioselective ring enlargements to form the corresponding thioesters. After warming of ...