Stereochemistry of the Diels-Alder Reaction of Butadiene with Cyclopropene
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.
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 http://dx.doi.org/10.1021/jo00283a018
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© 1989 American Chemical Society (ACS), All rights reserved.