Strain and reactivity: Electrophilic addition of bromine and tribromide salts to cyclic allenes

C Chiappe, A De Rubertis, H Detert…

Index: Chiappe, Cinzia; De Rubertis, Antonietta; Detert, Heiner; Lenoir, Dieter; Wannere, Chaitanya S.; Schleyer, Paul Von R. Chemistry - A European Journal, 2002 , vol. 8, # 4 p. 967 - 978

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Citation Number: 27

Abstract

Abstract The kinetics and the products of the bromination of several cyclic allenes, from C 9 to C 13 (1 a–e), with tetrabutylammonium tribromide (TBAT) and Br 2 have been investigated in 1, 2-dichloroethane (DCE) and methanol. The first product of the interaction between the allene and Br 2 is a 1: 1 π complex. The stability constant of this complex, determined at 25 C for allene 1 a, is 7.4 M− 1. The comparison of this value with those ...