Influence of structural features of tri-functionalized aryl phosphates on the outcome of the SRN1 process with stannyl anions. A DFT study

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

NEW JOURNAL OF CHEMISTRY

RSC

Lugar: Gainesville; Año: 2013 vol. 37 p. 1150 - 1156

1369-9261

Under irradiation, 1,3-bis(diethoxyphosphoryloxy)-4-chlorobenzene (2), 1,4-bis(diethoxyphosphoryloxy)- 3-chlorobenzene (3) and 1,3-bis(diethoxyphosphoryloxy)-5-chlorobenzene (4) react with trimethyltinsodium (1) in liquid ammonia giving entirely different distribution of stannylated products. These differences are explained through theoretical DFT studies. Experimental evidence for the involvement of an SRN1 mechanism was obtained