Tetrahedron

Reactions of vinylsilanes with lewis acid-activated iodosylbenzene: stereospecific syntheses of vinyliodonium tetrafluoroborates and their reactions as highly activated …

M Ochiai, K Sumi, Y Takaoka, M Kunishima, Y Nagao…

Index: Ochiai, Masahito; Sumi, Kenzo; Takaoka, Yoshikazu; Kunishima, Munetaka; Nagao, Yoshimitsu; et al. Tetrahedron, 1988 , vol. 44, # 13 p. 4095 - 4112

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Citation Number: 163

Abstract

Alkenyl (phenyl) iodonium tetrafluoroborates 3 were synthesized from alkenylsilanes 1 by the reaction with iodosylbenzene and boron trifluoride-diethyl ether or triethyloxonium tetrafluoroborate. The reaction proceeds stereospecifically with retention of configuration of 1. X-ray diffraction analysis of (4-tert-butylcyclohexenyl) phenyliodonium tetrafluoroborate (3b) revealed the highly ionic structure with the distorted T-shape arrangement. Iodonium ...