Synthesis of vinylstannanes. An unambiguous SRN1 mechanism

DORN, V. B.; M. T. LOCKHART; BADAJOZ, MERCEDES; CHOPA, ALICIA

Florianópolis-Brasil

Congreso; 7th Latin American Conference on Physical Organic Chemistry; 2003

7th Latin American Conference on Physical Organic Chemistry

There are multiple mechanistic routes of nucleophilic vinylic substitution reactions. Although rather scanty. there are antecedents in the literature concerning vinyl substitutions by the SRN1 mechanism. Triorganostannyl anions have proved to be excellent nucleophilcs in SRN1 reactions. Recently. we have described that the photochemically induced reaction of aryl diethyl phosphate esters with triorganostannyl anions in liquid ammonia. proceeds cleanly vja an SRN1 mechanism. Taking into account these antecedents: we have started a study of the reaction of vinyl diethyl phosphate esters (VinDEP) with trimthyl- (1) and triphenyltin anions (2) in liquid amonia. Now we report our first results of such study. in which it has been found that an SRN1 reaction does indeed ocurr under photostimulation.