Sulfuric acid-promoted rearrangement of 3-(N-acylamino)-substituted caran-4-one oximes

Sulfuric acid-promoted rearrangement of 3-(N-acylamino)-substituted caran-4-one oximes Full article

Journal

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

Output data

Year: 2005, Volume: 54, Number: 8, Pages: 1892-1899 Pages count : 8 DOI: 10.1007/s11172-006-0055-z

Tags

monoterpenoids; 3-carene; oximes; rearrangement; amides; sulfuric acid

Authors

Agafontsev A.M. ² , Tkachev A.V. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia

The rearrangement of 3-(N-acylamino)-substituted caran-4-one oximes in the presence of sulfuric acid affords 2-oxa-4-azabicyclo [3.3.1] non-3-en-6-one derivatives. 3-Aminocaran-4-one oximes, in which the amino group contains such substituents as acetyl, propionyl, chloroacetyl, 1-adamantylcarbonyl, benzoyl, 2-thienylcarbonyl, or anilinocarbonyl, undergo this reaction. N-Acyl derivatives of higher fatty (heptanoic and nonadecanoic) acids do not undergo this reaction. The reaction with D2SO4 leads to the replacement of all hydrogen atoms of the isopropyl group by deuterium. The mechanism of this rearrangement is proposed.

Agafontsev A.M. , Tkachev A.V.
Sulfuric acid-promoted rearrangement of 3-(N-acylamino)-substituted caran-4-one oximes
Russian Chemical Bulletin. 2005. V.54. N8. P.1892-1899. DOI: 10.1007/s11172-006-0055-z WOS Scopus РИНЦ

Агафонцев А.М. , Ткачев А.В.
Перегруппировка 3-n-ацилзамещенных производных оксима каран-4-она под действием серной кислоты
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2005. №8. С.1837-1844. РИНЦ

Published print:

Aug 1, 2005

Web of science	WOS:000235326900022
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