Reactions of 2,3,5-trichloro-4-hydroxycyclopent-2-en-1-one with dimethyl-and diethylamines and benzenethiol. Some aspects of stereochemical assignments in cyclopentenone chlorohydrins |
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| Authors: | N A Ivanova K S Kislitsina S A Torosyan M S Miftakhov |
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| Institution: | (1) Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia |
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| Abstract: | trans-2,3,5-Trichloro-4-hydroxycyclopent-2-en-1-one reacted with dimethyl-and diethylamines and sodium benzenethiolate in methanol to give the corresponding products of chlorine replacement at the sp 2-hybridized C3 atom via AdNE mechanism. The reactions were characterized by partial trans-cis isomerization. Assignment of configuration of isomeric cyclopentenone chlorohydrins on the basis of the NMR data is discussed. |
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