Tetrahedron letters

Comparison of the partition between polar and SET pathways in the S RN 1 mechanism for the nitronate and diethyldithiocarbamate anions. An unexpected result

K El Badraoui, M Chanon, D Merlet, K Chajara…

Index: Badraoui, K. El; Chanon; Merlet; Chajara; Courtieu Tetrahedron Letters, 1997 , vol. 38, # 5 p. 831 - 834

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Citation Number: 4

Abstract

Competition between SRN1 and SN2 mechanisms is discussed according to the stereochemical results in the alkylation of two anions by optically active α- chloroparanitrophenylethane1. In the reaction of 1 with the ambident anion of 2- nitropropane 2, competing SRN1 and SN2 processes take place, giving C-alkylation 3 with complete racemization and O-alkylation 4 products respectively. On the other hand, S- ...