Reactions of organic anions, 139. Vicarious nucleophilic substitution of hydrogen in 1,2,4-triazine derivatives
✍ Scribed by Rykowski, Andrzej ;Mąkosza, Mieczyslaw
- Publisher
- John Wiley and Sons
- Year
- 1988
- Tongue
- English
- Weight
- 473 KB
- Volume
- 1988
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Carbanions containing leaving groups at the carbanion centers react with 1.2.4-triazine and its derivatives according to the vicarious nucleophilic substitution scheme replacing hydrogen atoms in 5-, 3-. or &positions with the carbanion moiety. It is denionstrated that thc activity of various positions of the triazine ring toward nucleophilic substitution of hydrogen dccreases in this order. The reaction provides an elficient way of introduction of functionalized alkyl substituents into the triazine ring.
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## Abstract Reactions of carbanions of aryl chloromethyl and dichloromethyl sulfones 3 and 4 and __tert__‐butyl chloro‐ and dichloroacetates (5 and 6) with 1‐halo‐2,4‐dinitrobenzenes 1 and 2 proceed by nucleophilic replacement of a hydrogen atom. The S~N~Ar of the halogen atom occurs to a negligibl
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