Stereodynamics of substituted carboranes. I. 1,2-Bis(N,N-dimethylcarbamoyl)-1,2-dicarba-closo-dodecaborane(12) and 1,7-bis(N,N-dimethylcarbamoyl)-1,7-dicarba-closo-dodecaborane (12). Barriers to rotation and the aromaticity of the carborane cage

Bushweller, C. Hackett; Wang, Chih Y.; Dewkett, William J.; Anderson, Warren G.; Daniels, Stuart A.; Beall, Herbert

doi:10.1021/ja00812a051

Cited by 10 publications

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“…1 The reaction of lithiocarborane with amino-substituted acid chloride (Me 2 NC(O)Cl) also led to the formation of the corresponding carboranylamide. 12 Recently a new synthesis of carboranylamides has be reported by transition metal catalysis. For instance, Bregadze and Beletskaya et al 13 palladium catalyzed cross coupling of B-iodinated m-and pcarboranes with sodium amidates which afforded the corresponding carboranylamide products.…”

Section: Introductionmentioning

confidence: 99%

Syntheses and structural characterization of o-carboranylamides with direct cage–amide bond

et al. 2014

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Reactions of lithio-o-carborane with isocyanates under various conditions were studied, and the structural features of the resulting carboranylamides are described. The reactions of o-carborane (o-C2B10H12), n-BuLi (two equiv.) and two equiv. of (substituted) phenylisocyanate, pentylisocyanate and p-ethylphenylthioisocyanate in diethyl ether, respectively, led, after workup, to the corresponding mono-substituted carboranylamide 2a-g and carboranylthioamide 5 in low to moderate yields, and only with RNCO (R = Ph, m-MeOC6H4, pentyl) could disubstituted products 3a-c be isolated. The reaction with phenylisocyanate afforded the mono-amide and di-amide products in a ratio of approximately 1 : 2, whereas in the other two reactions the ratios are approximately 4 : 1 and 3 : 2, respectively. In tetrahydrofuran all the reactions attempted with RNCO (R = Ph, p-IC6H4, m-NCC6H4 and pentyl) gave more monoamide products than those in diethyl ether. With phenylisocyanate no diamide product was isolated and with pentylisocyanate the ratio between monoamide and diamide is approximately 3.5 : 1. The new carboranylamides were characterized by means of elemental analyses, IR and NMR spectroscopy and mass spectrometry, as well as single-crystal X-ray diffraction analyses of 2a-f, 3a and 5.

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Section: Introductionmentioning

confidence: 99%

Syntheses and structural characterization of o-carboranylamides with direct cage–amide bond

et al. 2014

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ChemInform Abstract: STEREODYNAMICS OF SUBSTITUTED CARBORANES PART 1, 1,2‐BIS(N,N‐DIMETHYLCARBAMOYL)‐1,2‐DICARBA‐CLOSO‐DODECABORANE(12) AND 1,7‐BIS(N,N‐DIMETHYLCARBAMOYL)‐1,7‐DICARBA‐CLOSO‐DODECABORANE(12), BARRIERS TO ROTATION AND THE AROMATICITY OF THE CARBORANE CAGE

Bushweller¹,

Wang²,

Dewkett³

et al. 1974

Chemischer Informationsdienst

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Stereodynamic effects in c-substituted derivatives of 1-(ortho-isopropylphenyl)-o-carborane

Калинин¹,

Antonovich²,

Finkel'shtein³

et al. 1979

J Struct Chem

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Stereodynamics of substituted carboranes. I. 1,2-Bis(N,N-dimethylcarbamoyl)-1,2-dicarba-closo-dodecaborane(12) and 1,7-bis(N,N-dimethylcarbamoyl)-1,7-dicarba-closo-dodecaborane (12). Barriers to rotation and the aromaticity of the carborane cage

Abstract: Durch Reaktion der C,C′‐Dilithioderivate der Carborane mit N,N‐Dimethylcarbamoyl‐ Chlorid in Äther bei 0°C werden die Titelverbindungen dargestellt.

Cited by 10 publications

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Syntheses and structural characterization of o-carboranylamides with direct cage–amide bond

Syntheses and structural characterization of o-carboranylamides with direct cage–amide bond

ChemInform Abstract: STEREODYNAMICS OF SUBSTITUTED CARBORANES PART 1, 1,2‐BIS(N,N‐DIMETHYLCARBAMOYL)‐1,2‐DICARBA‐CLOSO‐DODECABORANE(12) AND 1,7‐BIS(N,N‐DIMETHYLCARBAMOYL)‐1,7‐DICARBA‐CLOSO‐DODECABORANE(12), BARRIERS TO ROTATION AND THE AROMATICITY OF THE CARBORANE CAGE

Stereodynamic effects in c-substituted derivatives of 1-(ortho-isopropylphenyl)-o-carborane

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