Notiz zur [1,2]-Heterorest-Verschiebung in einem Sulfinamidin |
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Authors: | Johannes Häusler |
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Institution: | (1) Institut für Organische Chemie, Universität Wien, A-1090 Wien, Österreich |
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Abstract: | Reaction of methyl 1-pyrroline-2-carboxylate (3 a) with N,N -Ditosylsulphur-diimide affords the pyrrol-2-carboxylic acid derivative7. The sulfenamide function in7 is cleaved by trimethyl phosphite leading to8. Presumably the reaction sequence (3 a 7) takes its course via the sulfinamidine4 a and the rearrangement product5 a followed by elimination of tosylamide. An analogous reaction starting with the dimethyl-1-pyrrolin-2-carboxylate3 b yields the stable sulfinamidine4 b, which undergoes a rearrangement reaction with base producing6 b with the thioaminal5 b as the intermediate.Herrn Prof. Dr. Dr. h. c.K. Kratzl zum 70. Geburtstag herzlich gewidmet. |
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Keywords: | [1 2]-Rearrangement Sulfinamidine N N -Ditosyl-sulphurdi-imide" target="_blank">gif" alt="prime" align="BASELINE" BORDER="0">-Ditosyl-sulphurdi-imide |
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