Journal
ACCOUNTS OF CHEMICAL RESEARCH
Volume 35, Issue 1, Pages 12-18Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ar0100374
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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 voided, 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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