STEREOCHEMICAL ASPECTS OF THE DIELS-ALDER REACTION,
Abstract
In the Diels-Alder reaction of hexachlorocyclopentadiene and alpha-methyl-styrene, the cistrans ratio of deuterium in the beta-position of the alkene remains unchanged in the adduct. The reactions of cis- and trans-1,2-dichloroethylene with cyclopentadiene have been found to be at least 99.5% stereospecific. Since these systems were designed to favor the diradical intermediate which might be involved in a two-step mechanism, the observed high degree of specificity is best accounted for on the basis of a concerted, one-step mechanism. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Jan 01, 1965
- Accession Number
- AD0457062
Entities
People
- John D. Roberts
- Joseph B. Lambert
Organizations
- California Institute of Technology