Synthesis of protected benzenepolyselenols

J Org Chem. 2012 Oct 19;77(20):9397-400. doi: 10.1021/jo301447h. Epub 2012 Oct 1.

Abstract

Previously unknown benzenepolyselenols have been synthesized and isolated in their acetyl-protected form. The two molecules 1,3,5-tris(acetylseleno)benzene and 1,2,4,5-tetrakis(acetylseleno)benzene were synthesized by the reductive dealkylation in Na/NH(3) of 1,3,5-tris(tert-butylseleno)benzene and 1,2,4,5-tetrakis(tert-butylseleno)benzene, respectively. Hexakis(tert-butylseleno)benzene was also synthesized and structurally characterized by single-crystal X-ray diffraction, but it was not possible to isolate hexakis(acetylseleno)benzene. The synthetic methodology is likely to be useful in the synthesis of other areneselenols.