Title

Stereochemistry of the Diels-Alder Reaction of Butadiene with Cyclopropene

Abstract

1(E)-Deuteriobutadiene and cyclopropene react at 0°C to give 2-endo-deuteriobicyclo[4.1.0]hept-3-ene; 1-(Z)-deuteriobutadiene leads to the 2-exo-deuterio bicyclic product. Analysis of these products through 2H NMR spectroscopy reveals complete stereospecificity, indicating that the transition structure having an endo orientation of diene and cyclopropene is strongly favored over the alternative exo geometry. © 1989 American Chemical Society.

Department(s)

Chemistry

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 1989 American Chemical Society (ACS), All rights reserved.


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