CaltechAUTHORS
  A Caltech Library Service

Direct observation and retro-ene reaction of a propargylic diazene. Stereochemical assignment of monoalkyl diazenes

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. https://resolver.caltech.edu/CaltechAUTHORS:20170920-095832958

Full text is not posted in this repository. Consult Related URLs below.

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20170920-095832958

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/ja00182a035DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00182a035PublisherArticle
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.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
David and Lucile Packard FoundationUNSPECIFIED
Monsanto CompanyUNSPECIFIED
Rohm & Haas CompanyUNSPECIFIED
Eli Lilly and CompanyUNSPECIFIED
Hoffman-La Roche Inc.UNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Arnold and Mabel Beckman Laboratories of Chemical Synthesis8179
Issue or Number:26
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:03 Oct 2019 18:44

Repository Staff Only: item control page