Gas‐phase ion–molecule reactions of thioic and dithioic acid derivatives. Condensation reactions with alkenes and alkynes | Zendy

Paradisi Cristina | Zendy; Kenttämaa Hilkka | Zendy; Le Quang T. | Zendy; Caserio Marjorie C. | Zendy

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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.

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