On attempts at generation of carboranyl carbocation |
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Authors: | Tsuji Motonori |
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Institution: | Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. motonori@molfunction.com |
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Abstract: | We have synthesized all three possible isomers of C-hydroxycarborane from the corresponding amines via diazotization. The O-protonated C-hydroxycarboranes were characterized using the NMR spectrum measurements. Attempts at generating of carboranyl carbocations were carried out by the solvolyses of C-tosylates and C-triflates, as well as by treatment with superacids. Anchimeric assistance of both homoconjugative and hyperconjugative substituents was also investigated, as demonstrated by a successful strategy devised for the solvolytic generation of a phenyl cation. However, we have not been able to chemically provide any evidence of carboranyl carbocations, although the carboranyl carbocation may be an intermediate in the decomposition of the C-carboranediazonium ion. |
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