Chattopadhyaya, Jyoti B. ; Rama Rao, A. V. (1974) Electron-impact fragmentation of triaryl-s-trithianes: a novel skeletal rearrangement involving sulphur-sulphur bond formation Organic Mass Spectrometry, 9 (7). pp. 649-659. ISSN 0030-493X
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/oms.121...
Related URL: http://dx.doi.org/10.1002/oms.1210090704
Abstract
The mass spectral fragmentation of seven substituted 2,4,6-triaryl-s-trithianes has been studied and the fragmentation modes confirmed by deuterium labelling. Triphenyl-s-trithiane shows some interesting features in its mode of cleavage and does not eliminate S, S2, SH⋅, H2S or S2H⋅ from its molecular ion. The prominent radical ions in the mass spectrum are at m/e 180 (52.3%) and m/e 186 (45.2%), corresponding to stilbene and PhCHS3. Their compositions have been established by deuterium labelling and accurate mass measurements. The formation of stilbene indicates a relationship between pyrolytic and electron-impact studies. The origin of [PhCHS3]+⋅ suggests that one of the sulphur atoms attaches itself to the other two sulphur atoms in the molecular ion, eliminating a stilbene radical ion. The other important fragmentation corresponds to the monomer radical ion (thiobenzaldehyde) and the thiobenzoyl cation. Among the other substituted triaryl-s-trithianes with substituents such as chloro, methoxy, methylenedioxy and hydroxy groups on the phenyl ring (IV to IX), only the tris-(p-chlorophenyl)-s trithiane shows an insignificant molecular ion. Unlike the triphenyl derivative, the chloro, methoxy and methylenedioxy derivatives show the loss of HS⋅ and/or H2S from the molecular ion. The spectrum of tris-(p-hydroxyphenyl)-s-trithiane corresponds to the spectrum of p-hydroxythiobenzaldehyde.
Item Type: | Article |
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Source: | Copyright of this article belongs to John Wiley and Sons. |
ID Code: | 38941 |
Deposited On: | 05 May 2011 11:22 |
Last Modified: | 05 May 2011 11:22 |
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