Synthesis and thermal rearrangement of 5-diazomethyl-1,2,3-triazoles

Add time:08/29/2019    Source:sciencedirect.com

5-Diazomethyl-4-methoxycarbonyltriazoles are capable of undergoing ring-degenerate rearrangements (19 → 20) when a strong electron-withdrawing substituent (e.g. p-nitrophenyl or o,p-dinitrophenyl) is located at the N-1 position. Whereas the unrearranged diazomethyltriazole 19a decomposes thermally in benzene to give the cycloheptatriene 21a, the rearranged diazo compound 20b yields the norcaradiene 22b. Several methods are described for preparing the aldehydes 11 which are the precursors of the diazomethyltriazoles.

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