Article
Stereochemistry of the Diels-Alder Reaction of Butadiene with Cyclopropene
Journal of Organic Chemistry
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.
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.
Publication Date
10-1-1989
Publication Date
01 Oct 1989
Disciplines
Citation Information
John E. Baldwin and Prakash Reddy. "Stereochemistry of the Diels-Alder Reaction of Butadiene with Cyclopropene" Journal of Organic Chemistry Vol. 54 Iss. 22 (1989) p. 5264 - 5267 ISSN: 0022-3263 Available at: http://works.bepress.com/prakash-reddy/60/