Date of Thesis Acceptance
Major Department or Program
Marcus A. Juhasz
Palladium-catalyzed Rosenmund-von Braun conditions were applied to iodinated carboranes to prepare the first examples of cyano substituted derivatives of 1-carbacloso-dodecaborate(-1). Optimized microwave-assisted conditions with Pd(PPh3)2Cl2 and copper (I) cyanide formed [12-CB11H11CN]- , [7,12-CB11H10(CN)2] - , and [7,8,9,10,11,12- CB11H6(CN)6] - with great selectivity; products were purified and isolated as [Et4N]+ salts in up to 81% yield. The compounds were characterized by NMR (11B, 1H, and 13C), LCMS, and IR. Single crystal X-ray diffraction revealed the structure of the [Et4N][CB11H11CN] cage. Nitriles are known to undergo many organic reactions, and a preliminary investigation of hydrolysis of the cyano substituent revealed that the [12- CB11H11COOH]- cage can be formed. This work also reports improved microwave assisted synthesis of halogenated and alkynylated carboranes along with attempted reactions of these compounds.
Carboranes -- 1-carba-closo-dodecaborate, Chemical process -- Microwave irradiation, Boron, Halogenation, Alkynes -- alkynylation, Whitman College 2012 -- Dissertation collection -- Chemistry Department
Whitman Community Accessible Thesis
If you have questions about permitted uses of this content, please contact the ARMINDA administrator
In Copyright. URI: http://rightsstatements.org/vocab/InC/1.0/
This Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).