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Electron impact mass spectrometry of diethyl 2‐oxysubstituted alkylphosphonates—a remarkably regiospecific α‐cleavage
Author(s) -
Modro T. A.,
Mphahlele M. J.
Publication year - 1992
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.1210270112
Subject(s) - cleavage (geology) , chemistry , fragmentation (computing) , electron ionization , medicinal chemistry , mass spectrometry , ion , stereochemistry , organic chemistry , chromatography , ionization , fracture (geology) , computer science , operating system , geotechnical engineering , engineering
The major electron impact induced fragmentation of 2‐hydroxyphosphonic esters, XCH 2 CH(OH)CH 2 PO 3 Et 2 (and their O‐derivatives) involves the C(2)–C(3) α‐cleavage, yielding the XCH 2 · radical and the oxocarbonium ion, + HO = CHCH 2 PO 3 Et 2 . No evidence for a competitive C(1)–C(2) α‐cleavage was obtained, and the results suggest a stabilizing effect of the phosphonyl group on the α‐oxocarbonium system.