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On the Loss of SH• from the Molecular Ions of S-Alkyl Thioformates: Experimental Evidence for the Generation of Hydroxycarbenium Ions

✍ Scribed by Driss Lahem; Robert Flammang; Yves Van Haverbeke; Minh-Tho Nguyen

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 133 KB
Volume: 11
Category: Article
ISSN: 0951-4198
DOI: 10.1002/(sici)1097-0231(19970228)11:4<373::aid-rcm809>3.0.co;2-x

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✦ Synopsis

A series of S-alkyl thioformates, HC(O)SR, has been synthesized by formylation of alkane thiols and their behaviour upon electron impact has been investigated by using tandem mass spectrometry methodologies. When R > CH 3 , a prominent loss of a SH • radical is observed in the ion source as well as in the field-free regions. This reaction, which requires an important preliminary rearrangement of the molecular ion, gives hydroxycarbenium ions as evidenced by collisional-activation spectra and consecutive collisional-activation experiments. A mechanism involving ionized thietane intermediates is proposed.

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