1959
DOI: 10.1021/ja01527a030
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Isolation and Study of the Intermediate [Dimethyl-N-(2-cyano-2-propyl)-ketenimine] Formed in the Decomposition of α,α'-Azoisobutyronitrile

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Cited by 56 publications
(14 citation statements)
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“…The decomposition of AIBN follows a homolytic scission mechanism that has been extensively investigated [10][11][12][13]. AIBN decomposition normally occurs to an appreciable extent at temperatures greater than, say 50 • C, and its decomposition has been studied using techniques like ESR [14,15], NMR [16,17], FTIR [18], and UV spectroscopies [18,19].…”
Section: Introductionmentioning
confidence: 99%
“…The decomposition of AIBN follows a homolytic scission mechanism that has been extensively investigated [10][11][12][13]. AIBN decomposition normally occurs to an appreciable extent at temperatures greater than, say 50 • C, and its decomposition has been studied using techniques like ESR [14,15], NMR [16,17], FTIR [18], and UV spectroscopies [18,19].…”
Section: Introductionmentioning
confidence: 99%
“…The free cyanoisoprpoyl radicals can dimerize to give tetramethylsuccinodinitrile ( III ) and disproportionate to give isobutyronitrile ( IV ) and methacrylonitrile ( V ). The latter may react with further radicals to give tricyano‐2,3,5‐trimethylhexane ( VI )18–20 [eq. (2)]: …”
Section: Resultsmentioning
confidence: 99%
“…(3)]: The ketenimine ( VII ) is an unstable substance and at higher temperatures (i.e., ≥60°C) it rearranges to tetramethylsuccinodinitrile ( III ) 22. It is also capable of initiating vinyl polymerization20 (i.e., it is itself a source of radicals). Fission of a CN bond in the ketenimine to reform two radicals might be expected to occur at a rate almost equal to the rate of fission of CN bond in the AIBN because the adjacent bonds are similar 23…”
Section: Resultsmentioning
confidence: 99%
“…The Kelm collected is a water-white liquid which melts at 15° (determined using a crude method, could be off by several degrees) and having a refractive index, n 25° = 1.4475 (reported: m.p. 12.7°, n § 5 = 1.4473)(47). The yield of Kelm was raised from 10% by the first method to 30$ by the second method.…”
mentioning
confidence: 99%