Diphenyl methanol phenyl transfer

As previously observed for the diphenyl diselenide (Scheme 2) [24], Pandey has found that the phenyl alkyl selenides also can be transformed into the corresponding radical cations by photostimulated single electron transfer to 1,4-dicyanonaphthalene (DCN). These intermediates, as proposed above, suffer fragmentation to afford diphenyl diselenide and a carbocation, which can be trapped by a nucleophile. On the basis of these observations Pandey [121] described a sequential one-pot selenenylation-deselenenylation of alkenes in methanol using only catalytic amounts of diphenyl diselenide. An example is reported in Scheme 41 which illustrates the single steps of this process... 

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