Portal de Periódicos da CAPES

Solvolysis of Vinyl Iodonium Salts. New Insights into Vinyl Cation Intermediates

2001; American Chemical Society; Volume: 35; Issue: 1 Linguagem: Inglês

10.1021/ar0100374

1520-4898

Tadashi Okuyama,

Synthesis and Catalytic Reactions

Solvolysis of some vinyl iodonium salts carrying an excellent leaving group is examined, focusing on whether or not a classical primary vinyl cation can be generated. Formation of the primary cation is avoided, when possible, by participation of the beta substituent in the heterolysis to form a vinylenebenzenium ion or a secondary vinyl cation. Definitive evidence against a primary vinyl cation is provided by a chirality probe approach in the solvolysis of 4-methylcyclohexylidenemethyl iodonium salt.