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Stereochemical aspects of the Diels-Alder reaction

Lambert, Joseph B. and Roberts, John D. (1965) Stereochemical aspects of the Diels-Alder reaction. Tetrahedron Letters, 6 (20). pp. 1457-1463. ISSN 0040-4039. https://resolver.caltech.edu/CaltechAUTHORS:20151026-114006408

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Abstract

The mechanism of the Diels-Alder reaction has been a subject of intense interest for many years (1) and yet there is still substantial ambiguity concerning the timing of formation of the various bonds. In the present work we have examined the stereochemical pathways of systems designed to favor the diradical intermediate which might be involved in a two-step mechanism. The Woodward-Katz mechanism (1) embraces the salient features of both concerted and stepwise processes, although the authors seem to imply that, under favorable circumstances, a second barrier may intervene during the formation of the second bond, thus causing the overall process to be truly stepwise and perhaps not wholly stereospecific.


Item Type:Article
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http://dx.doi.org/10.1016/S0040-4039(00)90089-3DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403900900893PublisherArticle
Additional Information:© 1965 Pergamon Press Ltd. Received 17 February 1965; in revised form 12 March 1965. The authors are indebted to Mr. D. Kuwada for mass spectral measurements and to Dr. G. Binsch and Mr. T. Halgren for helpful discussions. This work was supported in part by the National Science Foundation and the Office of Naval Research.
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NSFUNSPECIFIED
Office of Naval Research (ONR)UNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry3210
Issue or Number:20
Record Number:CaltechAUTHORS:20151026-114006408
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151026-114006408
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61525
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 21:56
Last Modified:03 Oct 2019 09:09

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