TREATMENT OF DIMETHYL (+)-L-TARTRATE WITH SULFUR TETRAFLUORIDE

Article abstract of DOI:10.1016/S0022-1139(00)81331-7

Treatment of dimethyl (+)-L-tartrate (I) with sulfur tetrafluoride results in the formation of an intermediate, 2-fluoro-1,2-bis(methoxycarbonyl)ethyl fluorosulfite (II), which under the action of hydrogen fluoride, present in the reaction mixture, is converted into dimethyl (-)(2S:3S)-2-fluoro-3-hydroxysuccinate (III).The reaction of the latter with SF4 leads to dimethyl meso-2,3-difluorosuccinate (IV).The structure and configurations of the compounds obtained were established by 1H and 19F NMR.Treatment of dimethyl (+)-L-tartrate (I) with sulfur tetrafluoride in the presence of excessive hydrogen fluoride gave dimethyl meso-2,3-difluorosuccinate in 96percent yield.