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Synthesis and reactions of the cis- and trans-oxides derived from 3-(benzyloxy methyl)cyclohexene
- Source :
- Journal of Organic Chemistry. March 13, 1992, Vol. 57 Issue 6, p1713, 6 p.
- Publication Year :
- 1992
-
Abstract
- The synthesis of cis- and trans-3-(benzyloxymethyl)-1, 2-epoxycyclohexanes allows the study of their nucleophilic addition reactions. In the presence of a metallic salt catalyst, the cis-epoxide forms chelate intermediates which invite a nucleophilic attack on the C-1 oxirane carbon, resulting in ring cleavage. Its preference for chelation thus sterically directs the site of cleavage. The trans-epoxide, on the other hand, is prevented from undergoing chelation reactions due to its conformation. Its ring opening reactions are based on steric factors alone.
Details
- ISSN :
- 00223263
- Volume :
- 57
- Issue :
- 6
- Database :
- Gale General OneFile
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsgcl.13555408