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New Syntheses of Benzobarrelenes

Pu, Lin and Grubbs, Robert H. (1994) New Syntheses of Benzobarrelenes. Journal of Organic Chemistry, 59 (6). pp. 1351-1353. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20180413-144110586

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Abstract

New syntheses of both substituted and unsubstituted benzobarrelenes are described. Treatment of 3,5-cyclohexadiene-cis-1,2-diol with benzaldehyde dimethylacetal in the presence of a catalytic amount of p-toluenesulfonic acid gave 1,2-(benzylidenedioxy)-3,5-cyclohexadiene(2). Addition of benzynes to 2 provided 3 and 4. Treatment of 3 and 4 with excess LDA and potassium tert-butoxide afforded benzobarrelenes 1 and 5 in good yields.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://dx.doi.org/10.1021/jo00085a024DOIArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 1994 American Chemical Society. Received October 18, 1993. This work was supported by the Air Force Office of Scientific Research (AFOSR-88-0094). We thank Dr. Andy Muir of ICI Specialties and ICI Chemicals and Polymers, Runcorn, UK, for providing 3,5-cyclohexadiene-cis-1,2-diol.
Funders:
Funding AgencyGrant Number
Air Force Office of Scientific Research (AFOSR)AFOSR-88-0094
Issue or Number:6
Record Number:CaltechAUTHORS:20180413-144110586
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180413-144110586
Official Citation:New Syntheses of Benzobarrelenes Lin Pu and Robert H. Grubbs The Journal of Organic Chemistry 1994 59 (6), 1351-1353 DOI: 10.1021/jo00085a024
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:85848
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:13 Apr 2018 22:01
Last Modified:03 Oct 2019 19:36

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