PREPARATION AND INTERCONVERSION OF PHENYLSELENENYLATED AND ALKYLSELENENYLATED AROMATIC-COMPOUNDS

Phenylselenenyl and alkylselenenyl sulfates were found to efficiently and mildly introduce one or several phenylselenenyl or alkylselenenyl groups into activated aromatic or heteroaromatic compounds. When treat ed with methylselenenyl sulfate, veratrole and 2,2',3,3'-tetramethoxyb iphenyl afforded 2,3,7,8-tetramethoxyselenanthrene and 2,3,7,8-tetrame thoxy-dibenzoselenophene, respectively, via oxidative demethylation at selenium/cyclization. Phenyl-selenenylated thiophenes were selectivel y hydrodeselenenated at the 2- and/or 5-positions by treatment with th e appropriate amount of n-butyllithium at -78 degrees C followed by hy drolysis.