The Journal of Organic Chemistry

Selenium-stabilized carbocations. Formation of 2-(phenylseleno) allyl cations and their reactions with furan, pyrrole, and thiophene

S Halazy, L Hevesi

Index: Halazy, Serge; Hevesi, Laszlo Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5242 - 5246

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Citation Number: 19

Abstract

6-Bromovinyl selenides I (R,= H, CH,, CzH6; Rz= H, CH3; R3= H, CH3) have been prepared in excellent yields from allenes and benzeneselenenyl bromide. On treatment with silver perchlorate in nitromethane at-15" C and in the presence of a weak base, these 6- bromovinyl selenides reacted smoothly with electron-rich aromatic molecules such as furan, N-methylpyrrole, thiophene, or 1, 3, 5-trimethoxybenzene to give electrophilic substitution ...