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Electron ionization‐induced fragmentation of 3‐cyclopropanospiro and 3‐cyclobutanospiro derivatives of Benzo‐ and pyridosultams
Author(s) -
Danikiewicz Witold,
Wojciechowski Krzysztof,
Kosiński Szymon,
Olejnik Marian
Publication year - 2001
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.149
Subject(s) - chemistry , fragmentation (computing) , electron ionization , ion , ionization , aryl , thermal decomposition , molecule , medicinal chemistry , derivative (finance) , chemical ionization , stereochemistry , computational chemistry , organic chemistry , alkyl , computer science , financial economics , economics , operating system
Electron ionization‐induced fragmentations of 3‐cyclopropanospiro and 3‐cyclobutanospiro derivatives of selected benzo‐ and pyridosultams were studied and compared with the thermal decomposition of these compounds. 3‐Cyclopropanospirobenzosultams and the corresponding pyridosultams were found to be thermally stable up to 400 °C. At higher temperatures they eliminate an SO 2 molecule yielding several dimethylindole derivatives together with other isomeric compounds. Loss of SO 2 is also the main fragmentation process of the molecular ions of these compounds with the exception of the 4‐NO 2 derivative, for which elimination of CH 2 O is observed. 3‐Cyclobutanospirobenzosultams and ‐pyridosultams eliminate SO 2 on heating above 200 °C, yielding the corresponding 2‐aryl‐1,3‐butadienes. Under EI conditions expulsion of SO 2 from the molecular ions is also observed. However, elimination of C 2 H 4 is the dominant process except for the 5‐OCH 3 derivative. Copyright © 2001 John Wiley & Sons, Ltd.