Synthesis of bis(trimethylstannyl)aryl compounds via an SRN1 mechanism with intermediacy of monosubstitution products
1,2-Bis(trimethylstannyl)benzene (1) and 2,2′-bis(trimethylstannyl)-1,1′-binaphthyl (2), useful as intermediates in the preparation of bidentate Lewis acids, have been synthesized from simple phenols through a two-step sequence. Thus, 2-chlorophenol, 1,2-dihydroxybenzene, and binaphthol were convert...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2002 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/38322 |
| Acceso en línea: | http://hdl.handle.net/11336/38322 |
| Access Level: | acceso abierto |
| Palabra clave: | https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | 1,2-Bis(trimethylstannyl)benzene (1) and 2,2′-bis(trimethylstannyl)-1,1′-binaphthyl (2), useful as intermediates in the preparation of bidentate Lewis acids, have been synthesized from simple phenols through a two-step sequence. Thus, 2-chlorophenol, 1,2-dihydroxybenzene, and binaphthol were converted into the corresponding aryl diethyl phosphate esters 4-6, which on reaction with sodium trimethylstannide (3) in liquid ammonia, under irradiation, afforded 1 and 2, respectively, in good yields (66-82%). The results obtained clearly indicate that the reactions proceed through an SRN1 mechanism and involve the intermediacy of a monosubstitution product. |
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