Novel five- to ten-membered organoselenium heterocycles from the seienation of aromatic diols

Article abstract of DOI:10.1002/ejoc.201000075

Reaction of Woollins' reagent - WR, 2,4-bis(phenyl)-1,3- diselenadiphosphetane 2,4-diselenide [[PhP(Se)(μ-Se)}₂] - with aromatic diols in refluxing toluene afforded a series of novel five- to ten-membered phosphorus-selenium heterocycles 1-10 with an O-P(Se)-O or O-P(Se)-Se-P(Se)-O or O-P(Se)-OP(Se)-O linkage in 12-74% isolated yields. It was found that the diphosphorus species O-P(Se)-Se-P(Se)-O rings could be readily reduced into the monophosphorus species O-P(Se)O rings in almost quantitative yields via further reaction with another equivalent of corresponding aromatic diol. All new compounds have been characterized by IR ¹H NMR ¹³C NMR ³¹P NMR ⁷⁷Se NMR, mass spectrometry and elemental analysis or accurate mass measurement. Seven representative X-ray structures are reported.