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Mass spectrometry in structural and stereochemical problems—CLXXXV Effect of phenyl group in the mass spectra of trans ‐10‐phenyl‐2‐decalone and trans ‐10‐phenyldecalin
Author(s) -
Gray Robin T.,
Djerassi Carl
Publication year - 1970
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.1210030302
Subject(s) - alicyclic compound , fragmentation (computing) , chemistry , mass spectrum , stereochemistry , electron ionization , mass spectrometry , ion , group (periodic table) , metastability , deuterium , medicinal chemistry , organic chemistry , ionization , physics , chromatography , quantum mechanics , computer science , operating system
With the use of deuterium labeling and metastable ion measurements, the major fragmentation pathways of trans ‐10‐phenyl‐2‐decalone (II) have been deduced. A comparison with trans ‐10‐phenyldecalin (IV) demonstrated the almost complete domination of the phenyl group in directing the electron‐impact promoted decomposition of II. In fact, in contrast to the spectra of the methylated analogs, only one fragmentation pathway is uniquely associated with the carbonyl function. The substitution of a phenyl group at the ring junction in IV has permitted the recognition of definitive fragmentation pathways for this compound also. Such definition has not previously been possible for unsubstituted alicyclic hydrocarbons. The formation of an abundant tropylium ion from both II and IV has been examined, but its genesis is too complicated to be accurately defined from the labeling data at hand.