Myers, Andrew G. and Finney, Nathaniel S. (1990) Direct observation and retro-ene reaction of a propargylic diazene. Stereochemical assignment of monoalkyl diazenes. Journal of the American Chemical Society, 112 (26). pp. 9641-9643. ISSN 0002-7863. doi:10.1021/ja00182a035. https://resolver.caltech.edu/CaltechAUTHORS:20170920-095832958
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Abstract
Allylic and propargylic diazenes and their rearrangement by [3,3]-sigmatropic elimination of dinitrogen (retro-enc reaction) have been invoked in numerous organic transformations. As rearrangement uniformly occurs under the conditions of diazene formation, these hypothetical intermediates have not previously been observed, and fundamental questions regarding their stereochemistry (E vs Z) and reactivity remain. Employing a new method for diazene generation, we have been able to produce and study such an intermediate at low temperature and thereby address these issues of structure and mechanism, as described below.
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| Additional Information: | © 1990 American Chemical Society. Received August 1, 1990. We are grateful to Professor John D. Roberts for discussions concerning ^(15)N NMR spectroscopy and to Dr. David R. Wheeler for assistance with high-vacuum techniques. This research was generously supported by the National Science Foundation, the David and Lucile Packard Foundation, and the following industrial sponsors: Monsanto Company, Rohm & Haas Company, Eli Lilly and Company, and Hoffman-La Roche Inc. | ||||||||||||||
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| Issue or Number: | 26 | ||||||||||||||
| DOI: | 10.1021/ja00182a035 | ||||||||||||||
| Record Number: | CaltechAUTHORS:20170920-095832958 | ||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170920-095832958 | ||||||||||||||
| Official Citation: | Direct observation and retro-ene reaction of a propargylic diazene. Stereochemical assignment of monoalkyl diazenes. Andrew G. Myers and Nathaniel S. Finney. Journal of the American Chemical Society 1990 112 (26), 9641-9643 DOI: 10.1021/ja00182a035 | ||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||
| ID Code: | 81612 | ||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||||
| Deposited On: | 20 Sep 2017 19:04 | ||||||||||||||
| Last Modified: | 15 Nov 2021 19:44 |
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