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. doi:10.1021/ja01303a010. 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 | ||||||
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| Additional Information: | © 1936 American Chemical Society. Received August 10, 1936. Publication Date: December 1, 1936. | ||||||
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| Issue or Number: | 12 | ||||||
| DOI: | 10.1021/ja01303a010 | ||||||
| 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: | 16 Nov 2021 18:12 |
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