OXYMERCURATION OF Δ5-[2,2,2]-BICYCLOÖCTENE
- 1 September 1959
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 37 (9) , 1425-1431
- https://doi.org/10.1139/v59-209
Abstract
It has now been shown that an earlier assignment of configuration in which 1,4-↑↑-ethylene-Δ5-cyclohexenedicarboxylic acids and their derivatives were presumed to form with mercuric salts 5-↓-hydroxy-6-↓-anionomercuri-1,4-↑↑-ethylenecyclohexanedicarboxylic acid derivatives is incorrect. Instead 5-↓-hydroxy-6-↑-anionomercuri-1,4-↑↑-ethylenecyclohexanedicarboxylic acid derivatives are formed, similarly with the homologous 5-↓-hydroxy-6-↑-anionomercuri-1,4-methylenecyclohexane-2,3-dicarboxylic acid derivatives. This similarity is exemplified by comparable dipole moments. The exception is 5-↓-hydroxy-6-↓-chloromercuri-1,4-↑↑-methylenecyclohexane-2,3-↓↓-dicarboxylic acid, γ-lactone, which has a configuration opposite to all of the others of these series having boat-type cyclohexane ring conformations. The exception is attributed to steric effects.Keywords
This publication has 2 references indexed in Scilit:
- OXYMERCURATION OF BRIDGED CYCLOÖLEFINSThe Journal of Organic Chemistry, 1955
- Isomerism in the Diels—Alder Reaction. II. The Bromination of Diels—Alder Adducts1Journal of the American Chemical Society, 1953