Effect of structural features of tri-functionalized aryl phosphate isomers in the SRN1 behaviour. A DFT study

V.B. DORN; G.F. SILBESTRI; M.T. LOCKHART; A.B. CHOPA; A.B. PIERINI

internet

Congreso; International Electronic Conference on Synthetic Organic Chemistry (ECSOC-15); 2011

USC-MDPI-RSEQ

Under irradiation, the 1,3-bis(diethoxyphosphoryloxy)-4-chlorobenzene (3) and the 1,4- bis(diethoxyphosphoryloxy)-3-chlorobenzene (4) react with trimethyltinsodium (1) in liquid ammonia giving entirely different distribution of stannylated products. Evidence for the involvement of an SRN1 mechanism was obtained and through a theoretical DFT study we explain the differences observed between both isomers.3) and the 1,4- bis(diethoxyphosphoryloxy)-3-chlorobenzene (4) react with trimethyltinsodium (1) in liquid ammonia giving entirely different distribution of stannylated products. Evidence for the involvement of an SRN1 mechanism was obtained and through a theoretical DFT study we explain the differences observed between both isomers.4) react with trimethyltinsodium (1) in liquid ammonia giving entirely different distribution of stannylated products. Evidence for the involvement of an SRN1 mechanism was obtained and through a theoretical DFT study we explain the differences observed between both isomers.RN1 mechanism was obtained and through a theoretical DFT study we explain the differences observed between both isomers.