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The N,S-ketene acetals were synthesized in a three-step sequence starting from the corresponding cyclic amides, according to: Yde, B.; Yousif, N. M.; Pedersen, U.; Thomsen, I.; Lawesson, S.-O. Tetrahedron 1984, 40, 2047-2052. By thionation with Lawesson's reagent, the amides were converted into the thiocarbonyl compounds in excellent yields (85-95%). After methylation with methyl iodide and recrystallisation from acetone, 5-alkylated iodide salts (75-90%) were treated with potassium tert-butoxide to furnish the N,S-ketene acetals in moderate overall yields (35-65%).
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note
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Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-297966 (4a), CCDC-297967 (4c), CCDC-297968 (4e), CCDC-297970 (4h), CCDC-297969 (4i). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, U.K. (fax: + 44-1223/ 336-033; e-mail: deposit@ccdc.cam.ac.uk).
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