GAS-PHASE REACTIONS OF THE BENZYNE NEGATIVE-IONS

The reactions of o-, m- and p-benzyne anions and the phenide ion with a series of neutral reagents are described. The m- and p-benzyne anion s display similar behavior towards Bronsted acids, CS2, N2O, NO and O- 2, which is analogous to that of phenide ion but clearly different fro m that of o-benzyne anion. The strongly basic and nucleophilic charact er of m- and p-benzyne anions dominates their reactivity, and radical- type reactions are generally not observed. Novel bifunctional reaction s between m- and p-benzyne anions and both CS, and NO are observed in which two sequential S-atom abstractions and two NO additions, respect ively, take place. (C) 1998 John Wiley & Sons, Ltd.