Berson, Jerome A. and Dervan, Peter B. (1973) Rearrangement of trans-1,2-divinylcyclobutane and the energy surface of the dimers of butadiene. Journal of the American Chemical Society, 95 (1). pp. 267-269. ISSN 0002-7863. doi:10.1021/ja00782a061. https://resolver.caltech.edu/CaltechAUTHORS:20160516-100251258
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Abstract
In many thermal reactions, the experimentally determined heat of formation (ΔH_f^0) of the transition state is that predicted by bond additivity data to be appropriate for a species with one broken bond, a “diradical.”From the logical converse of this correspondence, a procedure has developed for estimation of ΔH_f^0 of a hypothetical diradical intermediate in a given reaction by measurement of the activation energy of a different reaction assumed to pass through the “same” intermediate. A recent important application has concerned the energy surface common to the dimers of butadiene, in which values of ΔH_f^0 for the hypothetical octa-1,7-diene-3,6-diyl diradicals *trans,trans*, *cis,-trans*, and *cis,cis* were estimated from various pyrolysis reactions (Scheme I) of trans- 1,2-divinylcyclobutane (1), 4-vinylcyclohexene (2), and cycloocta-1,5-diene (4).
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| Additional Information: | © 1973 American Chemical Society. Received July 21, 1972. Publication Date: January 1973. We are grateful for partial support of this work by grants from the National Science Foundation (GP-11017X and GP-33909X) and the Hoffmann-La Roche Foundation. Presented in part at the American Chemical Society 22nd National Organic Chemistry Symposium, Ann Arbor, Mich., June 1971, Abstracts, p 28. | |||||||||
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| Issue or Number: | 1 | |||||||||
| DOI: | 10.1021/ja00782a061 | |||||||||
| Record Number: | CaltechAUTHORS:20160516-100251258 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20160516-100251258 | |||||||||
| Official Citation: | Rearrangement of trans-1,2-divinylcyclobutane and the energy surface of the dimers of butadiene Jerome A. Berson and Peter B. Dervan Journal of the American Chemical Society 1973 95 (1), 267-269 DOI: 10.1021/ja00782a061 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 67119 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Victoria Brennan | |||||||||
| Deposited On: | 17 May 2016 21:29 | |||||||||
| Last Modified: | 11 Nov 2021 00:27 |
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