Selective deoxygenation of aryl selenoxides by triaryl phosphites. Evidence for a concerted transformation

Triaryl phosphites selectively reduce aryl selenoxides to selenides. The Hammett plot of the reactions of para-phenyl substituted triaryl phosphites with diphenyl selenoxide gave ρ=+2.3, whereas with bis(p-methoxyphenyl) selenoxide, ρ=−2.1. The results are consistent with a concerted mechanism for the oxygen transfer from Se to P.