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Single and double hydrogen rearrangements in the mass spectra of O‐ethyl, S‐alkyl methanephosphonothioates
Author(s) -
Tashma Zeev,
Katzhenler Jeoshua,
Deutsch Joseph
Publication year - 1973
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.1210070805
Subject(s) - chemistry , alkyl , branching (polymer chemistry) , mass spectrum , hydrogen , hydrogen atom , sulfur , thio , spectral line , electron ionization , carbon atom , stereochemistry , photochemistry , mass spectrometry , organic chemistry , ion , physics , ionization , chromatography , astronomy
Whereas the oxygen analogues of the title series gives rise to double hydrogen rearrangement on electron‐impact, alkylthiophosphonates show in addition a McLafferty rearrangement. The quantitative relationship between these two rearrangements in the thio series is dependent upon the chain length and branching on the alkyl group attached to sulphur. Comparison of the mass spectra of these compounds indicates that in the pathway of the double hydrogen rearrangement the hydrogen transferred to the sulphur atom originates primarily from the carbon δ to sulphur.