Phenols as Starting Materials for the Synthesis of Arylstannanes via SRN11
| Autor: | Alicia B. Chopa, Viviana Dorn, Maria T. Lockhart |
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| Rok vydání: | 2002 |
| Předmět: | |
| Zdroj: | Organometallics. 21:1425-1429 |
| ISSN: | 1520-6041 0276-7333 |
| DOI: | 10.1021/om010878e |
| Popis: | 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 S R N 1 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 1 leads to monostannylated product in fair to excellent yields (20-98%). Also, substrates containing two or three leaving groups react with 1 under irradiation, affording the corresponding di- or tristannylated aryl compounds. With tetraethyl m-phenylene bisphosphate (15), tetraethyl p-phenylene bisphosphate (21), (4-chlorophenyl)DEP (22), and 1,3,5-tris(diethylphospho)benzene (30), the di- or trisubstitution products 1,3-bis(trimethylstannyl)benzene (19) (79%), 1,4-bis(trimethylstannyl)benzene (23) (95 and 97%), and 1,3,5-tris(trimethylstannyl)benzene (31) (57%) are obtained, respectively. Also, the reaction of 6 and 7 with 2 leads to substitution products in quantitative yields, and the reaction of 21, 22, and (4-bromophenyl)DEP (24) with 2 affords 1,4-bis(triphenylstannyl)benzene (38) in high yields (70-100%). On the other hand, the results obtained in the photostimulated reaction of 24 and (4-iodophenyl)DEP (25) with 1, as well as in the reaction of 25 with 2, clearly indicate a fast HME reaction. |
| Databáze: | OpenAIRE |
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