Reaction of deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carbonyl chloride with aniline in pyridine gives predominantly deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carboxamide, accompanied by a small amount of the expected anilide. The results may be interpreted in terms of nucleophilic attack of aniline at the 2'-position of the N-(deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carbonyl)pyridinium intermediate, followed by ring-opening of the pyridine nucleus and recyclization.
CITATION STYLE
Yaguchi, K., & Endo, Y. (1999). Steric effects of polymethylcarboranes. Unusual reactivity of N-(deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carbonyl)pyridinium. Tetrahedron Letters, 40(41), 7351–7354. https://doi.org/10.1016/S0040-4039(99)01508-7
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