Oxosulphonium Ylides

Oxidation 205-213 /J-Oximinosulphoxides, chiral 336 Oxiranes 169 reactions of 305 synthesis of 639 2-Oxo-l,2,3-oxathiazolidines 71 /1-Oxosulphones, synthesis of 169 Oxosulphonium ylides, reactions of 219 /3-Oxosulphoxides reduction of 347-349 synthesis of 337-340... 

The mechanism of this modified procedure is thought to proceed in the same manner as that of the classic Swem oxidation with the formation of an oxosulphonium ylide. The structure of the oxidation reagent is depicted below. 

There is evidence, however, that these reactions may not involve conversion of the iodonium ylide into a carbene which then adds to the relevant substrate, but that this substrate is involved prior to cleavage of the carbon-iodine bond [136]. Other ylide interchange reactions which have been recorded include the conversions of various ylides into an oxosulphonium ylide by reaction with sulphur monoxide, generated in situ [141] ... 

Synthesis and Properties.—Additional details have been published on the preparation of oxosulphonium ylides from sulphoximides (see Chap. 2, Pt III, p. 144) and of phosphorylated oxosulphonium ylides. ... 

Michael addition to (dimethylamino)phenylvinyloxosulphonium salts (19) is thought to involve amino-oxosulphonium ylide intermediates such as (20). ... 

Pyrazole N-oxides (429) are formed by the action of nitrile oxides RCNO (R = Ph, Ac, or C02Et) on the imidoyl-substituted oxosulphonium ylide... 

Synthesis and Properties.—A number of heavily functionalized oxosulphonium ylides have been prepared, e.g. (19), which is converted by base into a thia-... 

Other substrates which have been allowed to react with oxosulphonium ylides are diphenylcyclopropenone and azomethine ylides. ... 

Alkoxysulphonium Ylides.—Alkoxysulphonium ylides are thought to be involved in the oxidation of alcohols with DMSO-related reagents, as demonstrated for the deuteriated form of Corey s iV-chlorosuccinimide-dimethyl sulphide reagent (23). Chlorosulphonium or chloro-oxosulphonium reagents Ra (0) -... 

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