Reactions of Organic Anions, 177. Vicarious Nucleophilic Substitution of Hydrogen, Bisannulation and Competitive Reactions of α-Haloalkyl Carbanions with Bicyclic Azaaromatic Compounds

1991 ◽  
Vol 124 (3) ◽  
pp. 577-585 ◽  
Author(s):  
Mieczyslaw Makosza ◽  
Jerzy Golinski ◽  
Stanislaw Ostrowski ◽  
Arvind B. Sahasrabudhe ◽  
Andrzej Rykowski
Keyword(s):  
Nucleophilic Substitution ◽  
Organic Anions ◽  
Nucleophilic Substitution Of Hydrogen ◽  
Vicarious Nucleophilic Substitution ◽  
Competitive Reactions

Reactions of organic anions. 174. Vicarious Nucleophilic Substitution of hydrogen (VNS) in nitrobenzofuroxans and the Boulton–Katritzky rearrangement of the VNS products

1990 ◽  
Vol 68 (12) ◽  
pp. 2239-2241 ◽  
Author(s):  
Stanisław Ostrowski ◽  
Krzysztof Wojciechowski
Keyword(s):  
Nucleophilic Substitution ◽  
Organic Anions ◽  
Nucleophilic Substitution Of Hydrogen ◽  
Tert Butyl ◽  
Vicarious Nucleophilic Substitution ◽  
Phenyl Sulfone

The Vicarious Nucleophilic Substitution of hydrogen in 4-nitrobenzofuroxan derivatives by carbanions of chloromethyl phenyl sulfone, chloromethyl p-tolyl sulfone, chloromethyl tert-butyl sulfone, and N,N-dimethyl chloromethane sulfonamide proceeds at positions 5 and 7. In some cases the Boulton–Katritzky rearrangement of the products obtained, leading to more stable 7-substituted isomers, was observed. Keywords: carbanions, nitrobenzofuroxans, sulfones, Vicarious Nucleophilic Substitution, Boulton–Katritzky rearrangement.

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