Tetrahedron

Etude stereochimique de l'alkylation d'anions par des derives p-nitrobenzyliques optiquement actifs: Competition SN2-SNR1

D Cabaret, N Maigrot, Z Welvart

Index: Cabaret, D.; Maigrot, N.; Welvart, Z. Tetrahedron, 1985 , vol. 41, # 22 p. 5357 - 5364

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Citation Number: 9

Abstract

Competition between SRN1, SN2 and SRN1 mechanisms is discussed according to the stereochemical results in the alkylation of anions by optically active secondary p-nitrobenzyl reagents. Results from alkylation of the anions of benzylcyanide C and α-aminonitrile A by p- nitrobenzyl chloride 2 rule out SN2 and SRN2 mechanisms. On the other hand, the SN2 process becomes exclusive in O-and C-alkylation of the acetoacetic ester anion B by the p ...

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