Murdoch University Research Repository

Welcome to the Murdoch University Research Repository

The Murdoch University Research Repository is an open access digital collection of research
created by Murdoch University staff, researchers and postgraduate students.

Learn more

The stereochemistry of SRN1 reactions in Nitroacenaphthenes

McLure, F.I. and Norris, R.K. (1987) The stereochemistry of SRN1 reactions in Nitroacenaphthenes. Australian Journal of Chemistry, 40 (3). p. 523.

Link to Published Version: https://doi.org/10.1071/CH9870523
*Subscription may be required

Abstract

The reaction of the 2-chloro-1,l-dialkyl-6-nitroacenaphthenes (1)-(3) with azide and p- toluenethiolate ions takes place by the SRN1 mechanism, to give the substitution products (27)-(32), despite the fact that the nitro group and the chlorine-bearing benzylic carbon are attached to different aromatic rings. The reaction of the stereoisomers (2) and (3) of 2-chloro-1-ethyl-1-methyl-6-nitroacenaphthene takes place through an effectively planar benzylic radical (35), which is preferentially attacked from the face remote from the a-ethyl group. The presence of geminal alkyl groups α to the reaction site in the rigid acenaphthene system restricts the scope of the substitution processes to sterically unhindered nucleophiles, and the reaction fails with reagents such as sodium p- toluenesulfinate (23) and the salts, (24) and (25), derived from 2-ethylmalononitrile and 2-nitropropane.

Item Type: Journal Article
Publisher: Commonwealth Scientific and Industrial Research Organization Publishing
Copyright: © 1987 CSIRO
URI: http://researchrepository.murdoch.edu.au/id/eprint/61823
Item Control Page Item Control Page