Uncatalyzed reactions of alpha-(trihaloethylidene)nitroalkanes with push-pull enamines: a new type of ring-ring tautomerism in cyclobutane derivatives and the dramatic effect of the trihalomethyl group on the reaction pathway / Korotaev Vladislav Yu,Barkov Alexey Yu,Slepukhin Pavel A.,Kodess Mikhail I.,Sosnovskikh Vyacheslav Ya // TETRAHEDRON LETTERS. - 2011. - V. 52, l. 44. - P. 5764-5768.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

A new type of ring-ring isomerism, which consists of the reversible transformation of cyclobutane derivatives into substituted 1,2-oxazine N-oxides was found and studied by NMR spectroscopy and X-ray diffraction analysis. The starting materials were prepared by the stereoselective reaction of alpha-(trifluoroethylidene)nitroalkanes, which react with ethyl beta-morpholino- and beta-piperidinocrotonates at the more nucleophilic alpha-position, whereas the reaction of alpha-(trichloroethylidene)nitroalkanes proceeds at the beta-methyl group to give the corresponding linear products. (C) 2011 Elsevier Ltd. All rights reserved.

Author keywords:

Conjugated nitroalkenes; Push-pull enamines; Cyclobutanes; 1,2-Oxazine N-oxides; Ring-ring tautomerism; Michael addition; 1D and 2D NMR spectroscopy; X-ray diffraction analysis CYCLIC NITRONIC ESTERS; CHAIN TAUTOMERISM; CYCLOADDITION REACTIONS; NITROOLEFINS; OLEFINS; 3,3,3-TRIFLUORO-1-NITROPROPENE; NUCLEOPHILES; VINYLAMINES

DOI:

10.1016/j.tetlet.2011.08.109

Web of Science ID:

ISI:000296168300012

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV 2
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	CYCLIC NITRONIC ESTERS; CHAIN TAUTOMERISM; CYCLOADDITION REACTIONS; NITROOLEFINS; OLEFINS; 3,3,3-TRIFLUORO-1-NITROPROPENE; NUCLEOPHILES; VINYLAMINES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	sosn1951@mail.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Funding-Acknowledgement	Russian Foundation for Basic Research {[}11-03-00126]
Funding-Text	This work was financially supported by the Russian Foundation for Basic Research (Grant 11-03-00126).
Number-of-Cited-References	38
Usage-Count-Since-2013	13
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	837CI