Flash-vacuum pyrolysis of 1-acylbenzotriazole: Direct observation of cyclopenta-2,4-dienylidenemethaneimines by tandem mass spectrometry and low-temperature infrared spectrometry
✍ Scribed by André Maquestiau; Didier Beugnies; Robert Flammang; Beat Freiermuth; Curt Wentrup
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 585 KB
- Volume
- 25
- Category
- Article
- ISSN
- 1076-5174
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✦ Synopsis
Abstract
A real‐time analysis of the flash‐vacuum pyrolysis products of 1‐acetylbenzotriazole (1) and 1‐benzoylbenzotriazole (2) was performed by tandem mass Spectrometry. In the temperature range 500‐600 °C, these compounds lose nitrogen, yielding N‐acetyl‐ and N‐benzoylcyclopenta‐ 2,4‐dienylidenemethaneimines (10 and 17, respectively). At higher pyrolysis temperatures, 1 gives 2‐methylbenzoxazole, cyanocyclopentadiene, methylcyanocyclopentadiene(s), benzonitrile and ketene, which were identified by collision‐activated dissociation mass Spectrometry. Low‐temperature infrared experiments confirmed the pyrolytic transformation 1(2) → 10(17) at mediated temperatures.