The 2-methylenimidazolines ImC(CN)2 (6a - c, Im = 1,3-dialkyl-4,5-dimethylimidazol-2-ylidene) are prepared by the reaction of the imidazolium salts [ImBr]Br (5) and malodinitrile while ImC{C(O)Ph}2 (7) is obtained from ImCH2 (2) and benzoic fluoride. Both the structural data of 6b, 6c, and 7 and the 13C NMR data demonstrate the influence of steric and electronic effects on the charge separation and the nonplanar arrangement of the substituents attached at the carbon atoms of the central olefinic bond
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Kühn et al. (2005) studied this question.