Mass spectral fragmentation of cis- and trans-1a,3-Disubstituted 1,1-Dichloro-1a,2,3,4-tetrahydro-1H-azirino[1,2-a] [1,5]benzodiazepines

✍ Scribed by Jiaxi Xu; Xinyu Zhang; Sheng Jin

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 54 KB
• Volume: 13
• Category: Article
• ISSN: 0951-4198
• DOI: 10.1002/(sici)1097-0231(19990730)13:14<1444::aid-rcm664>3.0.co;2-6

✦ Synopsis

The mass spectrometric behaviour of six cis-and trans-1a,3-disubstituted 1,1-dichloro-1a,2,3,4-tetrahydro-1H-azirino[1,2-a][1,5]benzodiazepines has been studied with the aid of mass-analysed ion kinetic energy spectrometry and exact mass measurements under electron impact ionization. All compounds show a tendency to eliminate a neutral propene or styrene molecule from the diazepine ring and to simultaneously eliminate a chlorine atom from the aziridine ring to yield azirino[1,2-b][1,3]benzimidazole ions, and to lose hydrogen chloride plus propene or styrene to give quinoxaline ions. All compounds also show a tendency to eliminate N=CCl 2 or HN=CCl 2 to produce dihydro-or tetrahydroquinoline ions, and to eliminate sequentially hydrogen chloride and a chlorine atom to yield pyrrolo[1,2-a][1,3]benzimidazole ions.