Abstract

GARCIA-MARTINEZ, Cirilo; PEREZ-ESPINO, Marco A.; CERVANTES-CUEVAS, Humberto  and  ESCALANTE-GARCIA, Jaime. Synthesis of α,β-Epoxysulfoxides: Thermodynamic Control in Base-induced Cyclization of Chlorohydrins Derived from α-Chlorobenzyl Phenyl Sulfoxide and Alkyl Aldehydes. J. Mex. Chem. Soc [online]. 2006, vol.50, n.3, pp.130-136. ISSN 1870-249X.

The preparation, purification and characterization of new sulfinylchlorohydrins and α,β-epoxy sulfoxides are reported. Sulfinylchlorohydrins were prepared by addition of lithium α-chlorobenzyl phenyl sulfoxide to acetaldehyde, propanaldehyde and butanaldehyde. Each aldehyde produced two diastereomeric chlorohydrins, which were characterized by IR and NMR. Relative configurations of the sulfinylchlorohydrins derived from acetaldehyde were established by X-ray diffraction. Experiments carried out at -70, -30, 0 and 25°C, showed that t-BuOK in THF induced isomerization of sulfinyl chlorohydrins faster than cyclization. Thus, trans- to cis-ratio of α,β-epoxy sulfoxides (85/15) was proportional to relative stability of sulfinylchlorohydrins.

Keywords : sulfinylchlorohydrins; Darzens reaction; α,β-epoxy sulfoxides; α-chlorobenzyl phenyl sulfoxide.

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