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Stereodistal Cope rearrangement of trans-1,2-dialkenylcyclobutanes

Berson, Jerome A. and Dervan, Peter B. (1972) Stereodistal Cope rearrangement of trans-1,2-dialkenylcyclobutanes. Journal of the American Chemical Society, 94 (25). pp. 8949-8950. ISSN 0002-7863. doi:10.1021/ja00780a074.

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Although stereoproximity of the ends (C_1 and C_6) of the biallyl system (schematically shown as 1) is required in the ordinary Cope rearrangement, there are a number of cases in which the process occurs despite a stereodistal relationship (2) imposed by the geometry of the reactant. A major mechanistic question is does the stereodistal reaction occur by an indirect mechanism requiring prior epimerization to the stereoproximal reactant, perhaps by way of a diradical intermediate 3, or can it occur directly, for example by closure of 3 at C_1 and C_6, to give Cope rearrangement product 4?

Item Type:Article
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Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 1972 American Chemical Society. Received August 14, 1972. Publication Date: December 1972. We thank the National Science Foundation (Grant No. GP-33909X) and the Hoffmann-La Roche Foundation for partial support of this work.
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Hoffmann-La Roche FoundationUNSPECIFIED
Issue or Number:25
Record Number:CaltechAUTHORS:20160516-100644365
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Official Citation:Stereodistal Cope rearrangement of trans-1,2-dialkenylcyclobutanes Jerome A. Berson and Peter B. Dervan Journal of the American Chemical Society 1972 94 (25), 8949-8950 DOI: 10.1021/ja00780a074
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:67122
Deposited By: Victoria Brennan
Deposited On:17 May 2016 21:23
Last Modified:11 Nov 2021 00:27

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