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Reactions of 3‐Nitro‐ν‐benzylideneacetophenone with Carbanions Containing Leaving Groups
Author(s) -
Makosza Mieczyslaw,
Krylova Irina V.
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199810)1998:10<2229::aid-ejoc2229>3.0.co;2-c
Subject(s) - chemistry , carbanion , nitro , intramolecular force , electrophilic substitution , medicinal chemistry , leaving group , electrophile , nucleophile , ring (chemistry) , stereochemistry , nucleophilic aromatic substitution , nucleophilic substitution , organic chemistry , catalysis , alkyl
3‐Nitro‐ω‐benzylideneacetophenone ( 1 ) reacts with carbanions containing leaving groups to give addition products to the electrophilic side chain. As a result of conjugated addition and subsequent intramolecular vicarious nucleophilic substitution of hydrogen (VNS) in the nitroaromatic ring of 1 in the position para to the nitro group, 4‐cyano‐7‐nitro‐3‐phenyl‐1,2,3,4‐tetrahydronaphthalen‐1‐one and 4‐cyano‐7‐nitro‐3‐phenylnaphth‐1‐ol are obtained. Smooth intramolecular VNS in the position para to the nitro group was observed for 4‐chloro‐1‐(3‐nitrophenyl)‐3‐phenyl‐4‐( p ‐tosyl)butanol.