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Mass spectrometry in structural and stereochemical problems—CLVIII electron impact promoted fragmentation of triphenylmethyl ethers
Author(s) -
Sheikh M. Younus,
Duffield A. M.,
Djerassi Carl
Publication year - 1968
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.1210010207
Subject(s) - chemistry , mass spectrum , electron ionization , fragmentation (computing) , moiety , deuterium , medicinal chemistry , ether , mass spectrometry , ion , alcohol , polyatomic ion , yield (engineering) , organic chemistry , photochemistry , ionization , physics , chromatography , quantum mechanics , computer science , operating system , materials science , metallurgy
The triphenylmethyl (trityl) moiety is frequently used for the protection of alcohols but the mass spectra of such trityl ethers have hitherto escaped scrutiny. It has now been found that triphenylmethyl derivatives of primary alcohols yield abundant molecular ions which permit the determination of the isotopic purity of the parent alcohol. Upon electron impact the triphenyl‐methyl entity directs the fragmentation of trityl ethers as demonstrated by a detailed study of n ‐pentyl trityl ether and its deuterated analogs. Ions formed by migration of phenyl groups were observed in the mass spectra of the trityl ethers investigated as well as in the spectrum of triphenyl‐methane itself.