Stereochemistry of the Diels-Alder Reaction of Butadiene with Cyclopropene

John E. Baldwin; Prakash Reddy

doi:10.1021/jo00283a018

Stereochemistry of the Diels-Alder Reaction of Butadiene with Cyclopropene

John E. Baldwin
, Prakash Reddy

Missouri University of Science and Technology

Research output: Contribution to journal › Article › peer-review

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 ² H 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.

Original language	American English
Journal	Journal of Organic Chemistry
Volume	54
DOIs	https://doi.org/10.1021/jo00283a018
State	Published - Oct 1 1989

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Chemistry

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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 2 H 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.",

author = "Baldwin, \{John E.\} and Prakash Reddy",

year = "1989",

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doi = "10.1021/jo00283a018",

language = "American English",

volume = "54",

journal = "Journal of Organic Chemistry",

issn = "1520-6904",

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T1 - Stereochemistry of the Diels-Alder Reaction of Butadiene with Cyclopropene

AU - Baldwin, John E.

AU - Reddy, Prakash

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N2 - 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 2 H 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.

AB - 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 2 H 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.

UR - https://scholarsmine.mst.edu/chem_facwork/1329

UR - https://doi.org/10.1021/jo00283a018

U2 - 10.1021/jo00283a018

DO - 10.1021/jo00283a018

M3 - Article

SN - 1520-6904

VL - 54

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

ER -

Stereochemistry of the Diels-Alder Reaction of Butadiene with Cyclopropene

Abstract

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