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- W2010659351 abstract "Substituent Transformations on Triaziridines Several novel triaziridines were prepared by substituent transformations starting from the known dialkyl-triaziridine-carboxylates 1a–c, with the aim to study the influence of the substitution pattern on the properties of the triaziridine ring. The dialkyl-triaziridines 2a–c were obtained by (t-BuO−)-mediated demethylation and decarboxylation and the dialkyl-triaziridine-methanols 4a–c by LiAlH4 reduction. Further reduction of the tosylates of 4a, b with LiAlH4 gave the methyl-dialkyl-triaziridines 3a, b. The dialkyl-triaziridines 2a, c could not be N-methylated directly with CH3I, but the anions 10a, c, obtained from 2a, c with CH3Li, yielded 3a, c. N-Methylation of 2a with (CH3)3OBF4 did not afford 3a but rather the methyl-triaziridinium salt 11. The dialkyl-triaziridine 2c has pKa > 14, its protonated species < 2. A concept that the electron pairs on the triaziridine N-atoms are more strongly localized than on amine N-atoms explains (a) that the dialkyl-triaziridine 2c is hardly basic, (b) that the LiAlH4 reductions of the esters 1 stop at the stage of the methanols 4, and (c) that the methanols 4a, b do not cleave like aminomethanols." @default.
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- W2010659351 date "1986-12-10" @default.
- W2010659351 modified "2023-09-26" @default.
- W2010659351 title "Triaziridine. 6. Mitteilung. Substituententransformationen an Triaziridinen" @default.
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- W2010659351 doi "https://doi.org/10.1002/hlca.19860690833" @default.
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