REACTION OF CERTAIN ALPHA,BETA-UNSATURATED TERPENIC OXIMES WITH SODIUM-NITRITE IN ACETIC-ACID - A FACILE SYNTHESIS OF ALLYLIC NITRO-COMPOUNDS

REACTION OF CERTAIN ALPHA,BETA-UNSATURATED TERPENIC OXIMES WITH SODIUM-NITRITE IN ACETIC-ACID - A FACILE SYNTHESIS OF ALLYLIC NITRO-COMPOUNDS Full article

Journal

Tetrahedron
ISSN: 0040-4020

Output data

Year: 1995, Volume: 51, Number: 6, Pages: 1789-1808 Pages count : 20 DOI: 10.1016/0040-4020(94)01057-7

Authors

Tkachev Alexey V. ¹ , Chibiryaev Andrey M. ¹ , Denisov Alexey Yu. ² , Gatilov Yuri V. ¹

Affiliations

1	Novosibirsk Institute of Organic Chemistry, Novosibirsk 630090, Russia
2	Novosibirsk Institute of Bioorganic Chemistry, Novosibirsk 630090, Russia

Reaction of nitrous acid with alpha,beta-unsaturated oximes having the structural fragment of 2-methyl-3-hydroxyimino-1-cyclohexene is described. A set of the oximes studied includes simple monocyclic derivatives (2-methyl-2-cyclohexenone oxime and carvone oxime) as well as more complex bicyclic compounds (car-2-en-4-one oxime and a-muurolen-3-one oxime). The reaction was shown to give allylic nitro compounds either with the retention of the carbon frame or with the rearranged skeleton. Chemical structure and stereochemistry of the products obtained are established by H-1, C-13 and N-14 NMR spectroscopy together with IR and UV data. Possible mechanisms of the reaction are discussed. Molecular mechanics and MNDO-calculations are used for the mechanistic study.

Tkachev A.V. , Chibiryaev A.M. , Denisov A.Y. , Gatilov Y.V.
REACTION OF CERTAIN ALPHA,BETA-UNSATURATED TERPENIC OXIMES WITH SODIUM-NITRITE IN ACETIC-ACID - A FACILE SYNTHESIS OF ALLYLIC NITRO-COMPOUNDS
Tetrahedron. 1995. V.51. N6. P.1789-1808. DOI: 10.1016/0040-4020(94)01057-7 WOS Scopus РИНЦ OpenAlex

Published print:

Feb 1, 1995

Web of science:	WOS:A1995QG19400020
Scopus:	2-s2.0-0028815974
Elibrary:	31160424
OpenAlex:	W2020790723

DB	Citing
Web of science	13
Scopus	10
Elibrary	19
OpenAlex	14