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Mechanism of the Thermal Isomerization of 5-Norbornene-2,3-endo-Dicarboxylic Anhydride

Baldwin, John E. and Roberts, John D. (1963) Mechanism of the Thermal Isomerization of 5-Norbornene-2,3-endo-Dicarboxylic Anhydride. Journal of the American Chemical Society, 85 (1). pp. 115-116. ISSN 0002-7863. doi:10.1021/ja00884a029. https://resolver.caltech.edu/CaltechAUTHORS:20151016-112438623

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Abstract

The thermal interconversions of α and β-1-hydroxydicyclopentadiene with syn- and anti-8-hydroxydicyclopentadiene, respectively, with retention of optical activity and analogous rearrangements have been considered in mechanistic descriptions of the Diels-Alder reaction. In the case of deuterium-labeled methacrolein dimer, an internal stereospecific pathway for rearrangement and complete dissociation of the dimer are very much in competition at 180°, and both reactions occur simultaneously. As was noted, the possibility that different energy paths are involved in the two processes remained unsettled.


Item Type:Article
Related URLs:
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http://dx.doi.org/10.1021/ja00884a029DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00884a029PublisherArticle
Additional Information:© 1963 American Chemical Society. Received November 15, 1962. Supported in part by the National Science Foundation.
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Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry2907
Issue or Number:1
DOI:10.1021/ja00884a029
Record Number:CaltechAUTHORS:20151016-112438623
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151016-112438623
Official Citation:Mechanism of the Thermal Isomerization of 5-Norbornene-2,3-endo-Dicarboxylic Anhydride John E. Baldwin and John D. Roberts Journal of the American Chemical Society 1963 85 (1), 115-116 DOI: 10.1021/ja00884a029
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61209
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:16 Oct 2015 21:35
Last Modified:10 Nov 2021 22:45

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