α-Trimethylsilyl-substitutedsulphoxides and sulphides undergo rearrangement with loss of the silyl group when treated respectively with trifluoroacetic anhydride and with N-halogenosuccinimide in the presence of trifluoroacetic acid, giving α-acyloxysulphides and α-halogenosulphides.
Treatment of the α-chloro-α-silyl sulphides (1) or (5) with trisubstitutedalkenes (6) in the presence of SnCl4 gave the vinylsulphides (7) or (8), the formation of which involves a carbenium ion rearrangement controlled by the silyl group.
Alkylative Lactonization of g,d-Unsaturated Esters with a-Chloro Sulfides. A Concise Synthesis of the Monoterpene Lactone from Chrysanthemum flosculosum L.
作者:Hiroyuki Ishibashi、Hiroshi Nakatani、Taru Su So、Toyokazu Fujita、Masazumi Ikeda