Synthesis of Protected Benzenepolyselenols

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/NH3 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.