Wagaman, Michael W. and Bellmann, Erika and Cucullu, Michèle and Grubbs, Robert H. (1997) Synthesis of Substituted Bicyclo[2.2.2]octatrienes. Journal of Organic Chemistry, 62 (26). pp. 9076-9082. ISSN 0022-3263. doi:10.1021/jo971039y. https://resolver.caltech.edu/CaltechAUTHORS:20180522-152355313
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Abstract
An efficient route to bicyclo[2.2.2]octatriene, barrelene, and substituted versions of this molecule has been developed starting from the benzene equivalent cis-3,5-cyclohexadiene-1,2-diol. Following the Diels−Alder reaction of this molecule with an activated acetylene, conversion of the diol to the final olefin was accomplished through formation of a thiocarbonate intermediate and subsequent reaction with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine (DPD). The synthesis developed allows a variety of barrelenes to be prepared in as few as three steps from commercially available starting materials.
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| Additional Information: | © 1997 American Chemical Society. Received June 10, 1997. Publication Date (Web): December 26, 1997. Financial support for this research was provided by the Office of Naval Research, the U.S. Air Force, and the Ballistic Missiles Defense Organization through an AASERT grant. We also thank Dr. D. G. H. Ballard and ICI for their gift of cis-3,5-cyclohexadiene-1,2-diol. | |||||||||
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| Issue or Number: | 26 | |||||||||
| DOI: | 10.1021/jo971039y | |||||||||
| Record Number: | CaltechAUTHORS:20180522-152355313 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20180522-152355313 | |||||||||
| Official Citation: | Synthesis of Substituted Bicyclo[2.2.2]octatrienes. Michael W. Wagaman, Erika Bellmann, Michèle Cucullu, and Robert H. Grubbs. The Journal of Organic Chemistry 1997 62 (26), 9076-9082 DOI: 10.1021/jo971039y | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 86559 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Tony Diaz | |||||||||
| Deposited On: | 24 May 2018 16:39 | |||||||||
| Last Modified: | 15 Nov 2021 20:39 |
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