Insertion reactions of 4H-imidazolylidenes into carbon-hydrogen bonds of alcohols was written by Kang, Uan G.;Shechter, Harold. And the article was included in Journal of the American Chemical Society in 1978.Computed Properties of C4H5N3O This article mentions the following:
Thermolysis of 4-diazoimidazole-5-carboxamide (I) at 60° in primary and secondary alcs. occurs with loss of N to give imidazole-4(5)-carboxamide (II) and RCOR1 (III; R = R1 = H, Me; R = Me, R1 = H) as major redox products and 5(4)-alkoxyimidazole-4(5)-carboxamides (IV; R = Me, Et, CHMe2, CMe3) by addition of the alcs. Photolysis of I at 25-30° differs from thermolysis in that N is rapidly expelled and 5(4)-(hydroxyalkyl)imidazole-4(5)-carboxamides (V and VI) are formed along with IV. V and VI result from insertion of 5-carboxamido-4H-imidazolylidene (VII) into the α and β-C-H bonds of the alcs. with subsequent H migration. Oxidn-reduction to II and VI also occurs upon photolysis of I in alcs. which undergo α-dehydrogenation. Photolysis of 5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide (VIII) results in expulsion of N and Me2NH and generation of VII. The behavior of I and VIII on photolysis in alcs. is similar. 2,5-Diphenyl-4H-imidazolylidene (IX), generated thermally from 5-diazo-2,4-diphenylimidazole at 60°, is a highly reactive carbene which inserts into the C-H bonds of cyclohexane and C6H6. Of significance is that IX inserts into a single C-H bond of Me3COH in 80% yield. Insertion reactions of carbenes into C-H bonds of alcs. may be of synthetic advantage. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Computed Properties of C4H5N3O).
1H-Imidazole-4-carboxamide (cas: 26832-08-6) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Computed Properties of C4H5N3O
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem