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- Title
[3+2] Cycloaddition of Dimethyl Acetylenedicarboxylate, Methyl Acrylate, and Ethyl Acrylate to 4,5-Dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1'-cyclohexane] N-Oxide.
- Authors
Varlamov, A. V.; Chernyshev, A. I.; Zubkov, F. I.; Turchin, K. F.; Levov, A. N.
- Abstract
The cycloaddition of methyl acrylate and ethyl acrylate to 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1'-cyclohexane] N-oxide proceeds without either regiospecificity or stereospecificity. Eight geometrical isomers of spiro[isoxazolidino[3,2-a]benz-2-azepine-5,1'-cyclohexane] were formed, of which several were isolated as pure samples. The cycloaddition of dimethyl acetylenedicarboxylate proceeds stereoselectively, leading to spiro[isoxazolino[3,2-a]benz-2-azepine-5,1'-cyclohexane] with cis arrangement of the protons at C(7) and C(11b).
- Subjects
ACRYLATES; RING formation (Chemistry); PROTONS; OXIDES; CHEMICAL reactions; ACRYLIC acid
- Publication
Chemistry of Heterocyclic Compounds, 2004, Vol 40, Issue 3, p364
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1023/B:COHC.0000028634.08685.99