Mechanism of the migration of the substituent in 1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole derivatives

Mechanism of the migration of the substituent in 1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole derivatives Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2010, Volume: 59, Number: 9, Pages: 1817-1826 Pages count : DOI: 10.1007/s11172-010-0318-6

Tags

2,3-dihydroisoxazole; 1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole; sigmatropic rearrangement; azomethine ylide; rate constants; quantum chemical calculations; DFT method; X-ray diffraction study

Authors

Chukanov N. V. ^1,2 , Popov S. A. ² , Drebushchak T. N. ^1,3 , Reznikov V. A. ^1,2

Affiliations

1	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, Inst Solid State Chem & Mechanochem, Novosibirsk 630128, Russia

The thermolysis of 1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole derivatives results in intramolecular rearrangements by two main pathways. One rearrangement affords azomethine ylide derivatives. Another rearrangement leads to the migration of the substituent from position 7a to the nitrogen atom. The rate constants of these reactions were determined. Quantum chemical calculations by the DFT method were carried out. Based on the data for the migration of the substituent, the concerted mechanism was proposed.

Chukanov N.V. , Popov S.A. , Drebushchak T.N. , Reznikov V.A.
Mechanism of the migration of the substituent in 1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole derivatives
Russian Chemical Bulletin. 2010. V.59. N9. P.1817-1826. DOI: 10.1007/s11172-010-0318-6 WOS Scopus РИНЦ

Чуканов Н.В. , Попов С.А. , Дребущак Т.Н. , Резников В.А.
Механизм миграции заместителя в производных 1,2,3,7a-тетрагидроимидазо[1,2- b]изоксазола
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2010. №9. С.1769. РИНЦ

Published print:	Sep 1, 2010
Published online:	Jan 26, 2011

Web of science	WOS:000286612600024
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