α-Vinylation of 1, 3-Dicarbonyl Compounds with Alkenyl (aryl) iodonium Tetrafluoroborates: Effects of Substituents on the Aromatic Ring and of Radical Inhibitors

…, T Shu, T Nagaoka, Y Kitagawa

Index: Ochiai, Masahito; Shu, Toshifusa; Nagaoka, Takema; Kitagawa, Yutaka Journal of Organic Chemistry, 1997 , vol. 62, # 7 p. 2130 - 2138

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Citation Number: 50

Abstract

Direct α-vinylations of enolate anions derived from 1, 3-dicarbonyl compounds with 4-tert- butyl-1-cyclohexenyl (aryl) iodonium 2 and 1-cyclopentenyl (aryl) iodonium tetrafluoroborates 3 are reported. Frequently, α-phenylations compete with the vinylations in the reaction of 1, 3-dicarbonyl compounds with alkenyl (phenyl) iodonium salts 2a and 3a. Use of alkenyl (p-methoxyphenyl) iodonium salts 2b and 3b, however, leads to selective α ...