Synthesis and application of new fluorinated ... - ELTE TTK TEO

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conditions (DMSO, 100 °C, and 3 h). Latter compounds were hydrogenated on a Parr instrument, under 3 atm hydrogen pressure to afford the appropriate amines (21a, 21b, 23). The reaction of thioacetate anion was successful with the primary (1°) tosylate 15 and the least hindered secondary (2°) mesylate 19a during one week reaction time with moderate yields, but the conversion of the more bulky mesylate 19b into the corresponding thioacetate failed. The tioacetates were hydrolized with aqueous NaOH in methanol under nitrogen atmosphere. 9 9 Z.-X. Jiang, Y. B. Yu, Tetrahedron, 2007, 63, 3982-3988.
These compounds was used in the synthesis of symmetrical and asymmetrical substituted imdazolium salts too. For the N-alkylation of imidazole we applied this substrate in threefold excess to avoid the formation of 1,3-dialkylated imidazolium salts. While the reaction of the reference 1° tosylate 15 gave the appropriate fluorous imidazole 26d in relatively good yield (62%) within 1 h heating at 100 °C in DMF, that of with the 2° mesylates 19a and 19b was rather sluggish and offered 26a and 26b, respectively, in 43 and 25% yields. We prepared a series of N,N’-dialkyl-imidazolium salts (29a,a-d; 29b,a-d; 29d,a-d; 29e,b-c) by the reaction of 1-alkyl-imidazoles (26a-b,d-e) with one equivalent of a different alkylating agent (13, 15, 27, 28) or symmetrically alkylated salts by the reaction of fluorous amines (21a,b) with formaldehyde and glyoxale.
Page 1 and 2: Synthesis and application of new fl
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Synthesis and application of new fluorinated ... - ELTE TTK TEO

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