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Stereochemical Relationships of the Isomeric 2,3-Butanediols and Related Compounds; Evidence of Walden Inversion

Wilson, Chester E. and Lucas, Howard J. (1936) Stereochemical Relationships of the Isomeric 2,3-Butanediols and Related Compounds; Evidence of Walden Inversion. Journal of the American Chemical Society, 58 (12). pp. 2396-2402. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20200410-104133807

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Abstract

This investigation has been undertaken for the purpose of synthesizing cis- and trans-2-butene in a pure state and of studying the Walden inversion. Incidentally, the work has constituted an independent confirmation of the observation that the butene produced in the dehydration of 1-butanol in the presence of sulfuric acid is approximately 68% trans-2-butene and 32% cis-2-butene. The reliability of this result has been questioned, on the basis that the dibromide method of analysis is faulty. This confirmation rests upon the observation that cis-2-butene is converted through the chlorohydrin to cis-2,3-epoxybutane and that the crude epoxybutane mixture obtained from the crude butene mixture is approximately 65% trons-2,3-epoxybutane and 35% cis-2,3-epoxybutane, with little or no 1,2-epoxybutane.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/ja01303a010DOIArticle
Additional Information:© 1936 American Chemical Society. Received August 10, 1936. Publication Date: December 1, 1936.
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Gates and Crellin Laboratories of Chemistry557
Issue or Number:12
Record Number:CaltechAUTHORS:20200410-104133807
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200410-104133807
Official Citation:Stereochemical Relationships of the Isomeric 2,3-Butanediols and Related Compounds; Evidence of Walden Inversion. Chester E. Wilson and Howard J. Lucas. Journal of the American Chemical Society 1936 58 (12), 2396-2402; DOI: 10.1021/ja01303a010
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:102484
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:10 Apr 2020 17:55
Last Modified:10 Apr 2020 17:55

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