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Stereospecific double rearrangement of trans-3,4-dimethyl-cis,trans-cycloocta-1,5-diene to cis-3,4-dimethyl-cis,cis-cycloocta-1,5-diene

Berson, Jerome A. and Dervan, Peter B. and Jenkins, Jerry A. (1972) Stereospecific double rearrangement of trans-3,4-dimethyl-cis,trans-cycloocta-1,5-diene to cis-3,4-dimethyl-cis,cis-cycloocta-1,5-diene. Journal of the American Chemical Society, 94 (21). pp. 7598-7599. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20160516-100848967

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Abstract

The chemistry of the highly strained cis,trans-cyclo-octa- 1,5-diene ring system* (1) is largely unexplored. Because there is a possibility that the corresponding 3,4-dimethyl derivatives 2 and 3 may be involved in the thermal nonboat, “crossover” rearrangement of cis- 1,2-cis,trans- and cis- 1,2-cis,cis-dipropenylcyclobutanes (cCT and cCC, respectively),3 we have carried out a study of the pyrolysis of trans-3,4-dimethyl-cis,trans- cyclo-octa- 1,5-diene (3). The present paper reports a new thermal rearrangement of this compound.


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http://dx.doi.org/10.1021/ja00776a065DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00776a065PublisherArticle
ORCID:
AuthorORCID
Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 1972 American Chemical Society. Received August 5, 1972. We thank the National Science Foundation (Grant No. GP-33909X) and the Hofmann-La Roche Foundation for partial support of this work.
Funders:
Funding AgencyGrant Number
NSFGP-33909X
Hofmann-La Roche FoundationUNSPECIFIED
Record Number:CaltechAUTHORS:20160516-100848967
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160516-100848967
Official Citation:Stereospecific double rearrangement of trans-3,4-dimethyl-cis,trans-cycloocta-1,5-diene to cis-3,4-dimethyl-cis,cis-cycloocta-1,5-diene Jerome A. Berson, Peter B. Dervan, and Jerry A. Jenkins Journal of the American Chemical Society 1972 94 (21), 7598-7599 DOI: 10.1021/ja00776a065
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ID Code:67123
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:16 May 2016 22:00
Last Modified:09 Nov 2017 00:04

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