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Chemical ionization induced competing and consecutive heterolytic ring cleavages in the mass spectra of substituted tetrahydro‐1,3,2‐oxazaphosphorin‐2‐oxides
Author(s) -
Kulkarni P. S.,
Gogte V. N.,
Modak A. S.,
Sahasrabudhe S. D.,
Tilak B. D.
Publication year - 1985
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.1210200705
Subject(s) - heterolysis , chemistry , nucleophile , mass spectrum , photochemistry , protonation , zwitterion , fragmentation (computing) , chemical ionization , mass spectrometry , ring (chemistry) , ionization , electrophile , ion , medicinal chemistry , computational chemistry , molecule , organic chemistry , catalysis , chromatography , computer science , operating system
The chemical ionization mass spectra of some substituted heterocyclic systems, viz. tetrahydro‐1,3,2‐oxazaphosphorin‐2‐oxides, reveal polar cycloreversion reactions. The zwitterion intermediate formed by the heterolysis of the CO bond undergoes stepwise clean heterolysis further resulting in the expulsion of the potential nucleophilic and electrophilic groups. The competitive and consecutive heterolysis of the ring bonds leads to the formation of the protonated phenylimine ions. Competing with heterolysis, elimination reactions involving hydrogen transfer leading to the formation of α‐phenylethyl ions are also observed. The chemical ionization mass spectrometry of the heterocyclic system shows many features of the Grob type of fragmentation mechanism.