Phenols as Starting Materials for the Synthesis of Arylstannanes via S<sub>RN</sub>1<sup>1</sup>
作者:Alicia B. Chopa、María T. Lockhart、Viviana B. Dorn
DOI:10.1021/om010878e
日期:2002.4.1
Phenols are converted into aryl diethyl phosphate esters (ArDEP), which on reaction with sodium trimethylstannide (1) or sodium triphenylstannide (2) in liquid ammonia afford arylstannanes by the SRN1 mechanism. Thus, the photostimulated reaction of phenylDEP (3), (4-methoxyphenyl)DEP (4), (4-biphenyl)DEP (5), (1-naphthyl)DEP (6), (2-naphthyl)DEP (7), and 2- (34), 3- (32), and (4-pyridyl)DEP (35) with
苯酚被转化为芳基二乙基磷酸酯(ArDEP),该芳基二乙基磷酸酯与三甲基锡钠(1)或三苯基锡钠(2)在液态氨中反应,通过S RN 1机理提供芳基锡烷。因此,苯基DEP (3),(4-甲氧基苯基)DEP(4),(4-联苯基)DEP(5),(1-萘基)DEP(6),(2-萘基)DEP(7)的光刺激反应。,以及2-(34),3-(32)和(4-吡啶基)DEP(35)与1导致单锡烷基化产品的收率相当高(20-98%)。同样,含有两个或三个离去基团的底物在辐射下与1反应,得到相应的二或三苯乙烯基化的芳基化合物。用四乙基米亚苯基二磷酸酯(15),四乙基p亚苯基二磷酸酯(21),(4-氯苯基)DEP(22),和1,3,5-三(diethylphospho)苯(30),所述二-或三取代产品1,3-双(三甲基锡烷基)苯(19)(79%),1,4-双(三甲基锡烷基)苯(23)(95和97%)和1,3,5-三(三