96797-16-9Relevant articles and documents
4-Lithio-1-tritylimidazole as a Synthetic Intermediate. Synthesis of Imidazole-4-carboxaldehyde
Kirk, Kenneth L.
, p. 57 - 59 (2007/10/02)
Reaction of 4-iodo-1-tritylimidazole with n-butyllithium at -79 deg, followed by rapid quenching of the reaction mixture with DMF, gives good yields of 1-tritylimidazole-4(5)-carboxaldehyde, the isolation of which demonstrates the intermediacy of 4-lithio-1-tritylimidazole.This species should be destabilized by repulsive interaction of the negative charge on C-4 with the adjacent lone pair electrons on N-3 (the ALP effect).The isolation of 1-tritylimidazole-4(5)-carboxaldehyde in good yield and the versatility of the aldehyde functionality make 4-lithio-1-tritylimidazole a useful synthetic intermediate.
