ISSN:
1434-193X
Keywords:
3-Nitro-ω-benzylideneacetophenone
;
Carbanions
;
Michael addition
;
Intramolecular vicarious nucleophilic substitution of hydrogen
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
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