Jump to main content
Jump to site search

Issue 13, 2014
Previous Article Next Article

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

Author affiliations

Abstract

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.

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

  • This article is part of the themed collection: Carboranes
Back to tab navigation

Supplementary files

Article information


Submitted
07 Oct 2013
Accepted
29 Nov 2013
First published
02 Dec 2013

Dalton Trans., 2014,43, 5083-5094
Article type
Paper

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

Y. Nie, Y. Wang, J. Miao, D. Bian, Z. Zhang, Y. Cui and G. Sun, Dalton Trans., 2014, 43, 5083
DOI: 10.1039/C3DT52785A

Social activity

Search articles by author

Spotlight

Advertisements