Vinyl iodonium salts photosolvolysis

General reactivities of vinyl iodonium salts are summarized, and reactions of cyclohexenyl, 1-alkenyl, styryl, and 2,2-disubstituted vinyl iodonium salts are discussed in relation to possible formation of vinyl cation intermediates. Primary vinyl cation cannot be generated thermally but rearrangement via neighboring group participation often occurs. Photosolvolysis to give primary vinyl cation is also discussed. 

The situation is quite different for the photochemical solvolysis reactions of vinyl iodonium salts. In all cases studied thus far these reactions involve direct, unassisted heterolytic cleavage of the vinylic C-I bond, yielding primary and endocyclic secondary vinyl cations. For example, photosolvolysis of ( )-styryl(phenyl)iodo-nium tetrafluoroborate (37) very efficiently yields the products resulting from heterolytic cleavage of the vinylic C-I bond, depicted in Scheme (Also... 

Photosolvolysis of ( )-styryl iodonium salt 26 also gave product distributions quite different from those obtained in thermal solvolysis.16,23 Quantum yields for the formation of photoproducts formed via heterolytic cleavage of the vinylic C-I bond of 26 in methanol and TFE at 20 °C are given in eq 20.23... 

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See also in sourсe #XX -- [ , , , ]

See also in sourсe #XX -- [ , , , ]

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