Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published October 1960 | public
Journal Article

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


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.

Additional Information

© 1960 American Chemical Society. Received April 2, 1960. This work has been supported by grants from the National Science Foundation.

Additional details

August 19, 2023
October 20, 2023