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 |
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Authors: | O. L. Epstein A. I. Savchenko O. G. Kulinkovich |
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Affiliation: | (1) Department of Organic Chemistry, Belorussian State University, 4 prosp. F. Skoriny, 220050 Minsk, Belarus |
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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. |
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Keywords: | cyclopropanation cyclopropanols titanium alkoxides Grignard reagents esters β -elimination titanacyclopropanes |
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