Stereochemistry of the Diels-Alder Reaction of Butadiene with Cyclopropene

Author

John E. Baldwin
Prakash Reddy, Missouri University of Science and TechnologyFollow

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.

Recommended Citation

J. E. Baldwin and P. Reddy, "Stereochemistry of the Diels-Alder Reaction of Butadiene with Cyclopropene," Journal of Organic Chemistry, vol. 54, no. 22, pp. 5264 - 5267, American Chemical Society (ACS), Oct 1989.

The definitive version is available at https://doi.org/10.1021/jo00283a018

Department(s)

Chemistry

International Standard Serial Number (ISSN)

0022-3263

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

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

Publication Date

01 Oct 1989