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The mechanisms of decomposition of the 1‐ and 2‐phenyltetralin radical cations
Author(s) -
Gallagher James J.,
Chess Edward K.,
Arghestani Saleh M.,
Gross Michael L.
Publication year - 1983
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.1210180307
Subject(s) - chemistry , decomposition , radical ion , styrene , carbon fibers , metastability , ion , methyl radical , photochemistry , medicinal chemistry , radical , organic chemistry , materials science , copolymer , polymer , composite number , composite material
Mechanisms for decomposition of 1‐ and 2‐phenyltetralins were investigated using low resolution mass spectrometry and metastable ion techniques. Four primary decompositions were observed for 1‐phenyltetralin radical cations: (1) the loss of C 6 H 6 via a 1,4‐elimination; (2) the elimination of ethene via competing losses from carbons 3 + 4 and carbons 2 + 3; (3) the loss of C 8 H 8 , probably through a stepwise Diels‐Alder cycloreversion to expel styrene; and (4) the loss of methyl radical involving carbon 2 and possibly carbon 4. Three major decompositions were observed for 2‐phenyltetralin radical cations: (1) the loss of C 8 H 8 , possibly through a Diels‐Alder cycloreversion to expel styrene; (2) the loss of C 6 H 6 via a 1,3 elimination; and (3) the loss of methyl radical from carbon 1. Various exchange reactions occur prior to these losses, but they proved to be incomplete even for metastable ions.