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 | ||||||
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| 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. | ||||||
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| 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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