Accession Number:

AD0457062

Title:

STEREOCHEMICAL ASPECTS OF THE DIELS-ALDER REACTION,

Descriptive Note:

Corporate Author:

CALIFORNIA INST OF TECH PASADENA GATES AND CRELLIN LABS OF CHEMISTRY

Personal Author(s):

• Lambert, Joseph B.
• Roberts, John D.

Report Date:

1965-01-01

Pagination or Media Count:

7.0

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

Descriptors:

• *DIENE SYNTHESIS
• STEREOCHEMISTRY
• SYNTHESIS(CHEMISTRY)
• ALKENES
• DEUTERIUM COMPOUNDS
• CYCLOPENTENES
• CHLORINE COMPOUNDS
• NUCLEAR MAGNETIC RESONANCE
• CHROMATOGRAPHIC ANALYSIS
• MOLECULAR ISOMERISM

Subject Categories:

Distribution Statement:

APPROVED FOR PUBLIC RELEASE