Improved syntheses of bis(ethynyl)-para-carboranes, 1,12-(RC C)(2)-1,12-C2B10H10 and 1,10-(RC equivalent to C)(2)-1,10-C2B8H8 (R = H or Me3Si).

Fox, M.A.; Baines, T.E.; Albesa-Jove, D.; Howard, J.A.K.; Low, P.J.

Abstract

Copper-mediated cross-coupling reactions of the 12-vertex and 10-vertex para carboranes, 1,12-C2B10H12 and 1,10-C2B8H10, with trans-1-iodo-2-chloroethene gave the bis(trans-2-chloroethenyl) carboranes, 1,12-(ClCHdouble bond; length as m-dashCH)2-1,12-C2B10H10 and 1,10-(ClCHdouble bond; length as m-dashCH)2-1,10-C2B8H8, respectively, in good yield. The molecular structures of both compounds were determined by X-ray crystallography, verifying the trans disposition of the chloride and carboranyl substituents across the double bonds. These vinyl carboranes can be converted to bis(ethynyl) carboranes, 1,12-(RCtriple bond; length of mdashC)2-1,12-C2B10H10 and 1,10-(RCtriple bond; length of mdashC)2-1,10-C2B8H8 (R = H or Me3Si), easily, and in high yields. These findings provide the most convenient routes to bis(ethynyl) carboranes from the commercially available carboranes, 1,12-C2B10H12 and 1,10-C2B8H10 reported to date.

Citation

Fox, M., Baines, T., Albesa-Jove, D., Howard, J., & Low, P. (2006). Improved syntheses of bis(ethynyl)-para-carboranes, 1,12-(RC C)(2)-1,12-C2B10H10 and 1,10-(RC equivalent to C)(2)-1,10-C2B8H8 (R = H or Me3Si). Journal of Organometallic Chemistry, 691(18), 3889-3894. https://doi.org/10.1016/j.jorganchem.2006.05.044

• Journal Article Type: Article
• Publication Date: 2006-09
• Journal: Journal of Organometallic Chemistry
• Print ISSN: 0022-328X
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 691
• Issue: 18
• Pages: 3889-3894
• DOI: https://doi.org/10.1016/j.jorganchem.2006.05.044
• Keywords: Carborane, Carbaborane, Alkyne, Alkene, Cross-coupling.
• Public URL: https://durham-repository.worktribe.com/output/1565348