Reactions of 2,4,6-Tri-t-butylphenyllithium with O-Alkyl Selenoformates: Intermediate Formation of 2,4,6-Tri-t-butylselenobenzaldehyde

Article abstract of DOI:10.1246/bcsj.59.2529

2,4,6-Tri-t-butylphenyllithium reacts with O-alkyl selenoformates (1) at three different sites (i.e., the selenoformyl carbon, the selenoformyl hydrogen, and the selenium) to give 1,3,5-tri-t-butylbenzene, 2,4,6-tri-t-butylbenzaldehyde, 6,8-di-t-butyl-3,4-dihydro-4,4-dimethyl-1H-2-benzoselenin (11), bis(2,4,6-tri-t-butylphenylmethyl) di(and tri) selenides, bis(2,4,6-tri-t-butylphenyl) diselenide, and dibutyl diselenide depending on the reaction conditions and the alkyl group in 1.The formation of 11 is explained in terms of the intermediacy of 2,4,6-tri-t-butylselenobenzaldehyde, which is trapped by condensation rection with butylamine leading to N-(2,4,6-tri-t-butylbenzylidene)butylamine.Mechanism for the formation of these products is also discussed.