Abstract

Abstract As part of a study attempting to elucidate the relation between the chemical structure of an azine and its pyrolysate, the pyrolyses of 2-acetylthiophene- (I) and 2-acetylfuranketazine (II) have been investigated. The pyrolysis of I at 270°C afforded principally nitrogen, ammonia, and 7-methy 1-5-(2-thienyl)-thieno[2,3-c]pyridine (III), plus lesser quantities of thiophenecarbonitrile and 2-acetylthiophene. The reductive desulfurization of III, followed by oxidation, afforded pyridine 2,4,6-tricarboxylic acid via 5-n-butyl-7-methyl-thieno[2,3-c]pyridine and 2-n-butyl-4-ethyl-6-methylpyridine. On the other hand, II was pyrolyzed to give nitrogen, ammonia, and tars as the major products, together with furan, furancarbonitrile, 2-acetylfuran, 5-(2-furyl)-7-methyl-furo[2,3-c]pyridine, and 2,4,6-tri(2-furyl)pyridine.

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