Synthesis of & ,B-Epoxysulfoxides: Thermodynamic Control in Base-induced Cyclization of Chlorohydrins Derived from α-Chlorobenzyl Phenyl Sulfoxide and Alkyl Aldehydes
The preparation, purification and characterization of newsulfinylchlorohydrins and α,β-epoxy sulfoxides are reported.Sulfinylchlorohydrins were prepared by addition of lithium α-chlorobenzyl phenyl sulfoxide to acetaldehyde, propanaldehyde andbutanaldehyde. Each aldehyde p...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2006 |
| País: | México |
| Institución: | Universidad Autónoma del Estado de Morelos |
| Repositorio: | Redalyc-UAEM |
| OAI Identifier: | oai:redalyc.org:47550313 |
| Acceso en línea: | https://www.redalyc.org/articulo.oa?id=47550313 |
| Access Level: | acceso abierto |
| Palabra clave: | Química α β Darzens reaction epoxy sulfoxides sulfinylchlorohydrins |
| Sumario: | The preparation, purification and characterization of newsulfinylchlorohydrins and α,β-epoxy sulfoxides are reported.Sulfinylchlorohydrins were prepared by addition of lithium α-chlorobenzyl phenyl sulfoxide to acetaldehyde, propanaldehyde andbutanaldehyde. Each aldehyde produced two diastereomeric chlorohydrins,which were characterized by IR and NMR. Relative configurationsof the sulfinylchlorohydrins derived from acetaldehyde wereestablished by X-ray diffraction. Experiments carried out at -70, -30,0 and 25°C, showed that t-BuOK in THF induced isomerization ofsulfinyl chlorohydrins faster than cyclization. Thus, trans- to cis-ratioof α,β-epoxy sulfoxides (85/15) was proportional to relative stabilityof sulfinylchlorohydrins. |
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