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The Mechanism of Decomposition of Azo Compounds. II. Cage Effects in the Decomposition of α,α-Azoisobutyronitrile and Related Compounds

Hammond, George S. and Wu, Chin-Hua S. and Trapp, Orlin D. and Warkentin, John and Keys, Richard T. (1960) The Mechanism of Decomposition of Azo Compounds. II. Cage Effects in the Decomposition of α,α-Azoisobutyronitrile and Related Compounds. Journal of the American Chemical Society, 82 (20). pp. 5394-5399. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20150302-094619530

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Abstract

The rate of formation of dimethyl-N-(2-cyano-2-propyl)-ketenimine (RR') from α, α'-azoisobutyronitrile (RN_2R) has been studied in carbon tetrachloride, benzene and styrene. A particularly detailed study was made in carbon tetrachloride solution at 62.5°. The yield of tetramethylsuccinonitrile (RR) from RN_2R in the presence of bromine has also been estimated. The results, coupled with other available information concerning the decomposition of RN_2R and RR', show that the ketenimine is produced by coupling of both primary and secondary decomposition fragments. Application of the theory of the cage effect as an important part of the mechanism of decomposition of azonitriles and ketenimines is justified.


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http://dx.doi.org/10.1021/ja01505a026 DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01505a026PublisherArticle
Additional Information:© 1960 American Chemical Society. Received April 2, 1960. This work has been supported by grants from the National Science Foundation.
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Caltech Gates and Crellin Laboratories of Chemistry2556
Record Number:CaltechAUTHORS:20150302-094619530
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20150302-094619530
Official Citation:The Mechanism of Decomposition of Azo Compounds. II. Cage Effects in the Decomposition of α,α-Azoisobutyronitrile and Related Compounds George S. Hammond, Chin-Hua S. Wu, Orlin D. Trapp, John Warkentin, and Richard T. Keys Journal of the American Chemical Society 1960 82 (20), 5394-5399 DOI: 10.1021/ja01505a026
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:55404
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:03 Mar 2015 23:46
Last Modified:11 Mar 2017 03:30

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