Solvolysis of vinyl iodonium salts. New insights into vinyl cation intermediates.
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.
Okuyama
Tadashi
T
Faculty of Science, Himeji Institute of Technology, Kamigori, Hyogo 678-1297, Japan. okuyama@sci.himeji-tech.ac.jp