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[reaction: see text] The reaction of benzyloxyfluorodiazirine (3) with SbF(5) in benzene gives PhCH(2)OCF, which undergoes SbF(5)-mediated fragmentation to PhCH(2)(+), CO, and SbF(6)(-); the benzyl cation alkylates benzene to yield diphenylmethane. Phenoxyfluorodiazirine (4) reacts with SbF(5) in benzene to give PhOCF and (ultimately) triphenylmethane by a pathway that avoids fragmentation.
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Moss et al. (2001) studied this question.
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