Unusual secondary to primary system rearrangement via ring opening of 1-(3-halopropylene)-4-methoxybenzenium ions

D Fain, JE Dubois

Index: Fain, Dominique; Dubois, Jacques-Emile Journal of Organic Chemistry, 1982 , vol. 47, # 25 p. 4855 - 4860

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Citation Number: 5

Abstract

The effect of electron-withdrawing groups on the ring opening of benzenium ions has been investigated by kinetics, equilibrium studies, and product analysis. The use of SnXl (X= Br or C1) compounds as highly ionizing solvents and as conveying agents of the X-nucleophile works quite well. 1, 2-Dihalo-3-(4-methoxyphenyl) propanes (2; X= Br or C1) and 1, 3-dihalo- 2-(4-methoxyphenyl) propanes (3; X= Br or C1) equilibrate at 100 “C in SnX'((X'= Br or C1) ...