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Mass spectral fragmentation of functionalized lanostanes‐I
Author(s) -
Dias Jerry Ray
Publication year - 1976
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.1210110402
Subject(s) - fragmentation (computing) , mass spectrum , chemistry , deuterium , hydrogen bond , hydrogen , spectral line , mass spectrometry , ionization , group (periodic table) , methyl group , computational chemistry , photochemistry , atomic physics , crystallography , molecule , physics , organic chemistry , ion , chromatography , computer science , operating system , astronomy
Mass spectra of various functionalized lanostanes and their deuterated analogs are compared. It is proposed that the transfer of a hydrogen from the 18‐methyl group to the 11‐oxo group via a McLafferty rearrangement is made geometrically possible by prior ionization of the 13,14 bond which allows an optimum interatomic distance between the oxygen and hydrogen to be acquired; the 8,9 double bond is a requisite for electronic induction of this specific process. Transfer of the hydrogen from the 7β‐hydroxy group to position 14 is implicated in the mass spectrum of 3β‐acetoxy‐7β‐hydroxy‐5α‐lanostan‐11‐one.