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. http://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.
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| 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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| Record Number: | CaltechAUTHORS:20151026-114006408 | |||||||||
| Persistent URL: | http://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: | 26 Oct 2015 21:56 |
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