Smith, Matthew R. Blake, Alexander J. Hayes, Christopher J. F. G. Stevens, Malcolm Moody, Christopher J. Carbene Reactivity of 4-Diazo-4<i>H</i>-imidazoles toward Nucleophiles and Aromatic Compounds Carbenes derived from diazoimidazolecarboxylates <b>4</b> 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 <b>7</b>. Reaction with pyridine leads to the first example of a pyridinium ylide <b>8</b> formed from an imidazolylidene carbene, whereas irradiation in hexafluorobenzene gives the imidazoazocine <b>11</b>, presumably by way of an initial norcaradiene intermediate. irradiation;diazoimidazolecarboxylate;Aromatic;imidazoazocine;Reactivity;insertion;hydrocarbon;arylimidazole derivatives 7. Reaction;pyridinium ylide 8;Carbene;norcaradiene;chloroimidazole;Nucleophile;solvent;amines;pyridine;Diazo;Dichloromethane;CompoundsCarbene;hexafluorobenzene;imidazolylidene carbene;trap 2009-12-18
    https://acs.figshare.com/articles/journal_contribution/Carbene_Reactivity_of_4_Diazo_4_i_H_i_imidazoles_toward_Nucleophiles_and_Aromatic_Compounds/2805586
10.1021/jo902165w.s003