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|Section2= }} ''tert''-Butyl isocyanide is an organic compound with the formula Me3CNC (Me = methyl, CH3). It is an isocyanide, commonly called isonitrile or carbylamine, as defined by the functional group C≡N-R. ''tert''-Butyl isocyanide, like most alkyl isocyanides, is a reactive colorless liquid with an extremely unpleasant odor. It forms stable complexes with transition metals and can insert into metal-carbon bonds.〔Malatesta, L. ''Isocyanide Complexes of Metals''Progress in Inorganic Chemistry, 1959, volume 1, 284-291.〕 ''tert''-Butyl isocyanide is prepared by a Hofmann carbylamine reaction. In this conversion, a dichloromethane solution of ''tert''-butylamine is treated with chloroform and aqueous sodium hydroxide in the presence of catalytic amount of the phase transfer catalyst benzyltriethylammonium chloride. :Me3CNH2 + CHCl3 + 3 NaOH → Me3CNC + 3 NaCl + 3 H2O ''tert''-Butyl isocyanide is isomeric with pivalonitrile, also known as ''tert''-butyl cyanide. The difference, as with all carbylamine analogs of nitriles, is that the bond joining the CN functional group to the parent molecule is made on the nitrogen, not the carbon. ==Coordination chemistry== By virtue of the lone electron pair on carbon, isocyanides serves as ligands in coordination chemistry, especially with metals in the 0, +1, and +2 oxidation states. ''tert''-Butyl isocyanide has been shown to stabilize metals in unusual oxidation states, such as Pd(I).〔Rettig, M.F.; Maitlis, P.M.; Cotton, F.A.; Webb, T.R. Tetrakis(''tert''-butyl isocyanide)Di-μ-chloro-dipalladium(I). ''Inorganic Syntheses'', 1990, 28, 110-113. ISBN 0-470-13259-0. 〕 : Pd(dba)2 + PdCl2(C6H5CN)2 + 4 ''t''-BuNC → ()2 + 2 dba + 2 C6H5CN ''tert''-Butyl isocyanide can form hepta-coordinate homoleptic complexes, despite having a large t-Bu group, which is held far away from the metal center because of the linearity of the M-C≡N-C linkages.〔Carnahan, E.M.; Protasiewicz, J.D.; Lippard, S.J. 15 years of reductive coupling: what have we learned? ''Acc. Chem. Res.'' 1993, 26, 90-97〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Tert-Butyl isocyanide」の詳細全文を読む スポンサード リンク
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