Alkenyl sulphones reactions

Sulphones - see also Acetoxysulphones, /1-Acyloxysulphones, a-Alkoxysulphones, a-Aminosulphones, Azidosulphones, Azosulphones, Azoxysulphones, co-Cyanosulphones, Dialkoxysulphones, a-Diazosulphones, Disulphones, Episulphones, Epoxysulphones, a-Halosulphones, Hydroxysulphones, / -Iminosulphones, Ketosulphones, a-Lithiosulphones, a-Nitrosulphones, /1-Oxosulphones, Poly(olefin suphonejs, Polysulphones, y-Siloxysulphones, Tetrahalosulphones, Trisulphones addition reactions of 642-649, 774-809 alkadienyl - see Alkadienyl sulphones alkenyl - see Alkenyl sulphones alkyl aryl - see Alkyl aryl sulphones alkylthiomethyl - see Alkylthiomethyl sulphones... 

Whereas oxygen nucleophiles gave poor yields of alkenylated products with alkenyl iodonium salts, the reactions with sulphur nucleophiles proceeded more efficiently, leading to unsaturated sulphides and sulphones. Thus, 4-t-butylcyclohexenyl phenyliodonium salts afforded with sodium thiophenoxide 4-t-butylcyclohexenyl phenyl sulphide (81%) [3] and with sodium phenylsulphinate the corresponding sulphone (29%) in the presence of 18-crown-6, the yield of the latter rose to 80% [45]. jS-Phenylsulphonylalkenyl iodonium salts with sodium phenylsulphinate at 0°C, without any catalyst, afforded Z-l,2-bis(phenylsulphonyl)alkenes, in high yield with retention of the stereochemistry [45] ... 

Alkylation of the sulphone (111) with Bu"Li-Me3SiCH2l gave the /8-silyl-sulphone (112) which with Bu NF gave ° 3-methylene-5a-cholestane (113). Alkenyl sulphoxides, such as (114), were reduced to the alkenyl sulphides, without double-bond isomerization, using EtNlgBr-Cul " and the terminal allene (115) was prepared by treatment of (114) with LTMP. Reaction of... 

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