Tandem pseudopericyclic processes in the cyclization of alpha-diazonitriles to 5-Halo-1,2,3-triazoles. Scope and limitations / Bakulev VA,Morzerin YY,Shafran YY,Mokrushin VS // ARKIVOC. - 2002. - V. , l. 8. - P. 166-179.

ISSN/EISSN:

нет данных / нет данных

Type:

Article

Abstract:

A series of alpha-carbonyl diazoacetonitriles has been synthesized and subjected to reaction with hydrogen halides. The scope and limitations of this reaction for preparing 5-halo-1,2,3-triazoles have been determined. The experimental energy of this cyclization is 15-20 Kcal mol(-1). A mechanism of this reaction consists of two steps-addition of HHal to alpha-carbonyl diazonitriles via a pseudopericyclic group transfer reaction leads to formation of intermediate alpha-diazohaloimines which in subsequent hetero-electrocyclic reactions afford 5-halo-1,2,3-triazoles. Indeed, the cyclization of alpha-carbonyl diazonitriles is a series of tandem pseudopericyclic processes.

Author keywords:

alpha-carbonyl diazoacetonitriles; 5-halo-1,2,3-triazoles; tandem pseudopericyclic processes AB-INITIO; HETEROCYCLIZATION; REACTIVITY; CONFORMATIONS; ISOMERIZATION; NITROSOKETENE; FORMYLKETENE; MINDO/3; DIAZO; ACID

DOI:

нет данных

Web of Science ID:

ISI:000179585500017

Соавторы в МНС:

Другие поля

Поле	Значение
Publisher	ARKAT FOUNDATION
Address	SCHANZENEGGSTRASSE 1, CH-8002 ZURICH, SWITZERLAND
Language	English
Keywords-Plus	AB-INITIO; HETEROCYCLIZATION; REACTIVITY; CONFORMATIONS; ISOMERIZATION; NITROSOKETENE; FORMYLKETENE; MINDO/3; DIAZO; ACID
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
ResearcherID-Numbers	Morzherin, Yury/M-7420-2013
ORCID-Numbers	Morzherin, Yury/0000-0002-1333-6676
Number-of-Cited-References	31
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	2
Journal-ISO	Arkivoc
Doc-Delivery-Number	621JP