The Mechanisms of Decomposition of the 1- and 2-Phenyltetralin Radical Cations

Article abstract of DOI:10.1002/oms.1210180307

Mechanisms for decomposition of 1- and 2-phenyltetralins were investigated using low resolution mass spectrometry and metastable ion tecniques.Four primary decompositions were observed for 1-phenyltetralin radical cations: (1) the loss of C6H6 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 C8H8, probably through a stepwise Diels-Alder cycloreversion to expel styrene; and (4) the loss of methyl radical involving carbon 2 and possible carbon 4.Three major decompositions were observed for 2-phenyltetralin radical cations: (1) the loss of C8H8, possible through a Diels-Alder cycloreversion to expel styrene; (2) the loss of C6H6 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.