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| Formato: | Artículo científico |
| Lenguaje: | en |
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Sociedad Química de México
2006
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| Acceso en línea: | https://www.redalyc.org/articulo.oa?id=47550313 |
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| _version_ | 1866585489440505856 |
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| author | Cirilo García-Martínez |
| author_facet | Cirilo García-Martínez |
| contents | Synthesis of & ,B-Epoxysulfoxides: Thermodynamic Control in Base-induced Cyclization of Chlorohydrins Derived from α-Chlorobenzyl Phenyl Sulfoxide and Alkyl Aldehydes Cirilo García-Martínez Marco A. Pérez-Espino Humberto Cervantes-Cuevas Jaime Escalante-García Multidisciplinaria (Ciencias Naturales y Exactas) α β Darzens reaction epoxy sulfoxides sulfinylchlorohydrins 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. 2006 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47550313 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.3 Vol.50 |
| format | Artículo científico |
| id | redalyc_47550313 |
| language | en |
| publishDate | 2006 |
| publisher | Sociedad Química de México |
| spellingShingle | Synthesis of & ,B-Epoxysulfoxides: Thermodynamic Control in Base-induced Cyclization of Chlorohydrins Derived from α-Chlorobenzyl Phenyl Sulfoxide and Alkyl Aldehydes Cirilo García-Martínez Multidisciplinaria (Ciencias Naturales y Exactas) α β Darzens reaction epoxy sulfoxides sulfinylchlorohydrins Synthesis of & ,B-Epoxysulfoxides: Thermodynamic Control in Base-induced Cyclization of Chlorohydrins Derived from α-Chlorobenzyl Phenyl Sulfoxide and Alkyl Aldehydes Cirilo García-Martínez Marco A. Pérez-Espino Humberto Cervantes-Cuevas Jaime Escalante-García Multidisciplinaria (Ciencias Naturales y Exactas) α β Darzens reaction epoxy sulfoxides sulfinylchlorohydrins 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. 2006 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47550313 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.3 Vol.50 |
| title | Synthesis of & ,B-Epoxysulfoxides: Thermodynamic Control in Base-induced Cyclization of Chlorohydrins Derived from α-Chlorobenzyl Phenyl Sulfoxide and Alkyl Aldehydes |
| topic | Multidisciplinaria (Ciencias Naturales y Exactas) α β Darzens reaction epoxy sulfoxides sulfinylchlorohydrins |
| url | https://www.redalyc.org/articulo.oa?id=47550313 |