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On the mechanism of titanium-catalyzed cyclopropanation of esters with aliphatic organomagnesium compounds. Deuterium distribution in the reaction products of (CD3)2CHMgBr with ethyl 3-chloropropionate in the presence of titanium tetraisopropoxide
Authors:O. L. Epstein  A. I. Savchenko  O. G. Kulinkovich
Affiliation:(1) Department of Organic Chemistry, Belorussian State University, 4 prosp. F. Skoriny, 220050 Minsk, Belarus
Abstract:The reaction of (CD3)2CHMgBr with ethyl 3-chloropropionate in the presence of catalytic amounts of Ti(OPr)4 results in (E)-1-(2-chloroethyl)-3,3-dideuterio-2-trideuterio-methylcyclopropanol and (CD3)2CDH, identified by mass spectrometry. The reaction mechanism is discussed. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 376–378, February, 2000.
Keywords:cyclopropanation  cyclopropanols  titanium alkoxides  Grignard reagents  esters  β  -elimination  titanacyclopropanes
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