EVIDENCE FOR THE TRANSITION FROM S-N TO ET MECHANISM IN THE REACTION OF ARENE RADICAL-ANION WITH ALKYL HALIDE EVOKED BY THE INTRODUCTION OFAN ELECTRON-WITHDRAWING SUBSTITUENT INTO RADICAL-ANION

The interaction of potassium salts of benzonitrile and 1,4-dicyanobenz ene radical anions with cyclopropylmethyl bromide provides benzylcyclo propane, in the first case, and 4-alkyl- benzonitriles together with 2 -alkyl-1,4-dicyanobenzenes containing both cyclopropylmethyl and it's isomeric 3-butenyl fragment, in the second case. These results provide evidence for the change of reaction mechanism from S-N to ET.