Journal of Organic Chemistry p. 4850 - 4853 (1980)
Update date:2022-09-26
Topics:
Sheradsky, Tuvia
Zbaida, David
The oxidation of anhydro-4-hydroxy-2,3,5-triarylthiazolium hydroxides (1) with m-chloroperbenzoic acid gave (in primary alcohols) 2,5-dialkoxy-2,3,5-triarylthiazolidin-4-ones (5) and N-aroylthiobenzanilides (6).Oxidation of anhydro-5-hydroxy-3-methyl-2-phenylthiazolium hydroxide (2) gave 3-methyl-2-phenylthiazolidine-4,5-dione (8) and N-formyl-N-methylthiobenzamide (9).The products arise from initial oxidations at the carbon atoms at position 5 of 1 and position 4 of 2, and transformation modes to the final products are discussed.These oxidations are the first examples of oxidative dipole extensions.
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(1981)
