Graduation Year

2012

Date of Thesis Acceptance

Winter 12-7-2012

Major Department or Program

Chemistry

Advisor(s)

Marcus A. Juhasz

Abstract

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.

Page Count

132

Subject Headings

Carboranes -- 1-carba-closo-dodecaborate, Chemical process -- Microwave irradiation, Boron, Halogenation, Alkynes -- alkynylation, Whitman College 2012 -- Dissertation collection -- Chemistry Department

Permanent URL

http://hdl.handle.net/10349/1187

Document Type

Whitman Community Accessible Thesis

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