4.7 Article

Carbene Reactivity of 4-Diazo-4H-imidazoles toward Nucleophiles and Aromatic Compounds

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 24, Pages 9372-9380

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo902165w

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Funding

  1. Marloes Technologies Ltd.

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Carbenes derived from diazoimidizolecarboxylates 4 under thermal or photochemical conditions undergo O-H and N-H insertion reactions with alcohols and amines, respectively, in moderate yield, in competition with reduction in good H-donor solvents. Dichloromethane reacts to give the corresponding 4-chloroimidazole. Aromatic hydrocarbons are excellent traps for the imidazolylidene carbene and lead to a range of arylimidazole derivatives 7. Reaction with pyridine leads to the first example of a pyridinium ylide 8 formed from an imidazolylidene carbene, whereas irradiation in hexanuorobenzene gives the imidazoazocine 11, presumably by way of an initial norcaradiene intermediate.

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