Rearrangement of trans-1,2-divinylcyclobutane and the energy surface of the dimers of butadiene
- Creators
- Berson, Jerome A.
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Dervan, Peter B.
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).
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.Additional details
- Eprint ID
- 67119
- DOI
- 10.1021/ja00782a061
- Resolver ID
- CaltechAUTHORS:20160516-100251258
- NSF
- GP-11017X
- NSF
- GP-33909X
- Hoffmann-La Roche Foundation
- Created
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2016-05-17Created from EPrint's datestamp field
- Updated
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2021-11-11Created from EPrint's last_modified field