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High resolution mass spectrometry in molecular structure studies—VI: The fragmentation of amaryllis alkaloids in the crinine series. Compounds bearing a hydroxyl substituent at C‐11 (and some 11‐oxo derivatives)
Author(s) -
Longevialle P.,
Fales H. M.,
Highet R. J.,
Burlingame A. L.
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.1210070406
Subject(s) - substituent , fragmentation (computing) , chemistry , mass spectrometry , stereochemistry , hydrogen atom , fast atom bombardment , computational chemistry , organic chemistry , chromatography , group (periodic table) , computer science , operating system
High resolution mass spectral fragmentation patterns of Amaryllidaceae alkaloids in the crinine series bearing a substituent at C‐11 have been investigated, as well as certain isotopically labeled derivatives. The substituent at C‐11 governs almost entirely the fragmentation pattern of these bases due to the ability of the hydroxylic hydrogen atom to rearrange. In contrast to the bases lacking this hydrozyl substituent, stereochemistry exerts a profound influence on the fragmentation.