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- W2014142761 abstract "The reaction of 9H-fluorene-9-thione (1) with the cis- and trans-isomers of dimethyl 1-(4-methoxyphenyl)aziridine-2,3-dicarboxylate (cis- and trans-2, resp.) in xylene at 110° yielded exclusively the spirocyclic cycloadduct with trans- and cis-configurations, respectively (trans- and cis-3, resp.; Scheme 1). Analogously, less-reactive thioketones, e.g., thiobenzophenone (5), and cis-2 reacted stereoselectively to give the corresponding trans-1,3-thiazolidine-2,4-dicarboxylate (e.g., trans-8; Scheme 2). On the other hand, the reaction of 5 and trans-2 proceeded in a nonstereoselective course to provide a mixture of trans- and cis-substituted cycloadducts. This result can be explained by an isomerization of the intermediate azomethine ylide. Dimethyl 1,3-thiazolidine-2,2-dicarboxylates 14 and 15 were formed in the thermal reaction of dimethyl aziridine-2,2-dicarboxylate 11 with aromatic thioketones (Scheme 3). On treatment of 14 and 15 with Raney-Ni in refluxing EtOH, a desulfurization and ring-contraction led to the formation of azetidine-2,2-dicarboxylates 17 and 18, respectively (Scheme 4)." @default.
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- W2014142761 date "2002-07-01" @default.
- W2014142761 modified "2023-10-14" @default.
- W2014142761 title "1,3-Thiazolidine-dicarboxylates from Thioketones and Thermally Generated Azomethine Ylides" @default.
- W2014142761 doi "https://doi.org/10.1002/1522-2675(200207)85:7<2056::aid-hlca2056>3.0.co;2-o" @default.
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