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Gas‐phase ion–molecule reactions of thioic and dithioic acid derivatives. Condensation reactions with alkenes and alkynes
Author(s) -
Paradisi Cristina,
Kenttämaa Hilkka,
Le Quang T.,
Caserio Marjorie C.
Publication year - 1988
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210230705
Subject(s) - chemistry , fourier transform ion cyclotron resonance , molecule , alkyl , ionic bonding , ion , ion cyclotron resonance , photochemistry , condensation reaction , fragmentation (computing) , imide , medicinal chemistry , organic chemistry , catalysis , cyclotron , computer science , operating system
A Fourier transform–ion cyclotron resonance study of thioacyl compounds as binary mixtures with unsaturated hydrocarbons has revealed that thioacetylium ions CH 3 CS + generated by electron fragmentation fail to thioacyl‐ate even the most reactive aromatic hydrocarbons. Among the hydrocarbons studied, only 3‐hexyne and 2,4‐dimethyl‐2,5‐hexadiene were observed to react with CH 3 CS + . Apart from proton‐transfer reactions, the major ionic reaction of thioesters with arenes, alkynes and alkenes is condensation of the molecular ion of one component, usually the ester, with a neutral molecule of the other, resulting in the cleavage of the SC alkyl bond of the thioester. The nature of this reaction is discussed and a possible mechanism is suggested.