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.
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Tadashi Okuyama (2001) studied this question.
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