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Rearrangements in the electron‐impact induced fragmentation reactions of 5‐alkylthio‐1,3,4‐thiadiazolyl‐2‐amines
Author(s) -
Barnes C. S.,
Goldsack R. J.,
Rao Ravindra Pratap
Publication year - 1971
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.1210050310
Subject(s) - homologous series , alkyl , chemistry , olefin fiber , fragmentation (computing) , ethylene , polyatomic ion , medicinal chemistry , mass spectrum , ion , electron ionization , stereochemistry , organic chemistry , biology , catalysis , ionization , ecology , polymer
The low resolution mass spectra of a number of homologous 5‐alkylthio‐1,3,4‐thiadiazolyl‐2‐amines have been determined. With the methylthio compound the only significant loss from the molecular ion is the sulphydryl radical. As the homologous series is ascended this reaction becomes less important and is insignificant with the butylthio isomers. The ethylthio compound suffers extensive loss of ethylene and when the alkyl group contains three or more carbon atoms the main reaction is always loss of the olefin coresponding to the alkyl group.All of the n‐alkylthio compounds showed in addition loss of methylthio radical from the molecular ion. A mechanism is proposed and comparisons made with alkyl phenyl thioethers and alkylthio substituted heterocycles.