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. https://resolver.caltech.edu/CaltechAUTHORS:20160516-100644365
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Abstract
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?
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| 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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| Issue or Number: | 25 | |||||||||
| DOI: | 10.1021/ja00780a074 | |||||||||
| Record Number: | CaltechAUTHORS:20160516-100644365 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20160516-100644365 | |||||||||
| 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 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Victoria Brennan | |||||||||
| Deposited On: | 17 May 2016 21:23 | |||||||||
| Last Modified: | 11 Nov 2021 00:27 |
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