Published December 1, 1990
| public
Journal Article
Direct observation and retro-ene reaction of a propargylic diazene. Stereochemical assignment of monoalkyl diazenes
- Creators
- Myers, Andrew G.
- Finney, Nathaniel S.
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.
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.Additional details
- Eprint ID
- 81612
- Resolver ID
- CaltechAUTHORS:20170920-095832958
- NSF
- David and Lucile Packard Foundation
- Monsanto Company
- Rohm & Haas Company
- Eli Lilly and Company
- Hoffman-La Roche Inc.
- Created
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2017-09-20Created from EPrint's datestamp field
- Updated
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2021-11-15Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Arnold and Mabel Beckman Laboratories of Chemical Synthesis
- Other Numbering System Identifier
- 8179