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Mass spectral fragmentation patterns of 1a,3‐diaryl‐1,1,4,4‐tetrachloro‐1a,2,3,4‐tetrahydro‐1 H ‐azirino[2,1‐ e ][1,6]benzothiazocines
Author(s) -
Xu Jiaxi,
Lan Ruoxi,
Jin Sheng
Publication year - 1999
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/(sici)1097-0231(19990730)13:14<1511::aid-rcm677>3.0.co;2-5
Subject(s) - chemistry , ion , fragmentation (computing) , ring (chemistry) , mass spectrum , chlorine , yield (engineering) , electron ionization , mass spectrometry , molecule , polyatomic ion , hydrogen atom , chloride , ionization , medicinal chemistry , photochemistry , organic chemistry , alkyl , materials science , chromatography , computer science , metallurgy , operating system
The mass spectrometric behaviour of three 1a,3‐diaryl‐1,1,4,4‐tetrachloro‐1a,2,3,4‐tetrahydro‐1 H ‐azirino[2,1‐ e ][1,6]benzothiazocines has been studied with the aid of mass‐analyzed ion kinetic energy spectro‐metry and exact mass measurements under electron impact ionization. All compounds show a tendencyto eliminate a neutral substituted/unsubstituted 1,1‐dichlorostyrene from the eight‐membered thiazocine ring to yield azirino[2,1‐ c ][1,4]benzothiazine ions, which can then lose a chlorine radical and a sulfuratom to form azirino[2,1‐ c ][1,4]benzothiazine ions and dihydroquinoline ions. All compounds could also eliminate a chlorine radical plus hydrogen chloride, stepwise or consecutively, to undergo a ring enlargement rearrangement to produce nine‐membered 1,7‐benzothiazonine ions. The [M + − Cl] ions could undergo a four‐membered ring rearrangement to yield 1,5‐benzothiazepine ions by loss of 1,1‐dichlorostyrene or styrene ions and HCl, and undergo α , α‐cleavage to form benzothiazine ions by loss of arylchlorocyclopropane. The [M + − Cl − HCl] ions could further eliminate some atoms, small molecules or molecular fragments to form some abundant fragment ions. Copyright © 1999 John Wiley & Sons, Ltd.