Deoxygenative vs. vicarious nucleophilic substitution of hydrogen in reactions of 1,2,4-triazine 4-oxides with alpha-halocarbanions / Kozhevnikov DN,Rusinov VL,Chupakhin ON,Makosza M,Rykowski A,Wolinska E // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2002. - V. , l. 8. - P. 1412-1416.

ISSN/EISSN:

1434-193X / нет данных

Type:

Article

Abstract:

The 3,6-diaryl- 1,2,4-triazine 4-oxides la-e undergo a nucleophilic substitution of hydrogen with the alpha-halomethyl aryl sulfones 2, 3 and 7 by two alternative pathways: vicarious nucleophilic substitution (VNS) and/or an intramolecular deoxygenative process, The former pathway is found to dominate in the reaction of 1 with bromomethyl tolyl sulfone (7) yielding the 5-tosylmethyl-1,2,4-triazine 4-oxides 6, while the reaction with the chloromethyl aryl sulfones 2 and 3 leads to the 5-arylsulfonylchloromethyl-1,2,4-triazines 4 and 5, respectively, as the products of deoxygenative substitution. The reaction of 6-phenyl-1,2,4-triazine 4-oxide (11) with the chloromethyl aryl sulfones 2 and 3 proceeds differently. At low temperature (-75 C) the products of the VNS reaction at position 5 (6f and 12f) are formed, At room temperature the 7-chloro-1-hydroxy-3-phenyl-7-(aryisulfonyl)-1,4,5-triaza- hepta-1,3,6-trienes 10f and 11f are obtained by addition of the carbanions 2 and 3 in the 3-position, followed by the ring opening of the resulting a adduct. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Author keywords:

aromatic substitution; nucleophilic substitution; nitrogen heterocycles; carbanions; C-C coupling POTASSIUM-PERMANGANATE; CHICHIBABIN AMINATION; PHENYL SULFONES; ORGANIC-ANIONS; LIQUID-AMMONIA; REAGENT

DOI:

нет данных

Web of Science ID:

ISI:000175093200010

Соавторы в МНС:

Другие поля

Поле	Значение
Month	APR
Publisher	WILEY-V C H VERLAG GMBH
Address	PO BOX 10 11 61, D-69451 WEINHEIM, GERMANY
Language	English
Keywords-Plus	POTASSIUM-PERMANGANATE; CHICHIBABIN AMINATION; PHENYL SULFONES; ORGANIC-ANIONS; LIQUID-AMMONIA; REAGENT
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
ResearcherID-Numbers	Makosza, Mieczyslaw/A-6383-2008
Number-of-Cited-References	17
Usage-Count-Since-2013	4
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	543GN