Synthesis of bis(trimethylstannyl)aryl compounds via an SRN1 mechanism with intermediacy of monosubstitution products

Abstract

1,2-Bis(trimethylstannyl)benzene (1) and 2,2′-bis(trimethylstannyl)-1,1′-binaphthyl (2), useful as intermediates in the preparation of bidentate Lewis acids, have been synthesized from simple phenols through a two-step sequence. Thus, 2-chlorophenol, 1,2-dihydroxybenzene, and binaphthol were converted into the corresponding aryl diethyl phosphate esters 4-6, which on reaction with sodium trimethylstannide (3) in liquid ammonia, under irradiation, afforded 1 and 2, respectively, in good yields (66-82%). The results obtained clearly indicate that the reactions proceed through an SRN1 mechanism and involve the intermediacy of a monosubstitution product.