Journal article
The stereochemistry of SRN1 reactions in Nitroacenaphthenes
Australian Journal of Chemistry, Vol.40(3)
1987
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.
Details
- Title
- The stereochemistry of SRN1 reactions in Nitroacenaphthenes
- Authors/Creators
- F.I. McLure (Author/Creator)R.K. Norris (Author/Creator)
- Publication Details
- Australian Journal of Chemistry, Vol.40(3)
- Publisher
- Commonwealth Scientific and Industrial Research Organization Publishing
- Identifiers
- 991005545233207891
- Copyright
- © 1987 CSIRO
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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- Citation topics
- 2 Chemistry
- 2.1 Synthesis
- 2.1.824 Solvolysis
- Web Of Science research areas
- Chemistry, Multidisciplinary
- ESI research areas
- Chemistry