Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Mechanism of Transylidation of Stable Sulfonium Ylids with Alkyl Sulfides in the Presence of Catalytic Disulfides
Haruo MatsuyamaHiroshi MinatoMichio Kobayashi
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1973 Volume 46 Issue 12 Pages 3828-3830


In the presence of bis(trifluoromethyl) disulfide, methylphenylsulfonium bis(methoxycarbonyl)methylid is readily attacked by a nucleophile (an alkyl sulfide or a pyridine) and the corresponding new ylid is produced. In the NMR spectrum of a mixture of an ylid, an alkyl sulfide, and a catalytic disulfide, a remarkable broadening in the signals of the α-hydrogen of the sulfide was observed. A mechanism is suggested, which involves a complex from the two reactants and the catalyst.

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