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A study on the organic chemistry of tin and tin hydride radical chemistry reports on the results of the synthesis and analysis of eight members of a new family of highly fluorinated tin hydrides as reagents for radical reactions. It provides some of the first detailed information on how the nature and composition of fluorous chains affects the reactivity and solubility of fluorous reagents. Experimental methodology and results are presented.

The use of supercritical CO2 as a reaction solvent has been limited, and a solution could be to use radical reactions that proceed well in nonpolar solvents. The simple reduction of bromoadamantane to adamantane, conducting radical reactions by initial pressurization to 850 psig, was investigaed. Tris(perfluorohexylethyl)tin hydride was soluble under reaction conditions, although a mixture with tributyltin hydride was not homogenous.

The preparation and characterization of tris 2-(perfluorohexyl)ethyl tin hydride as a fluorous agent in combinatorial synthesis using organic substrates is discussed. The tin hydride was obtained from 2-perfluorohexyl-1-iodoethane via a series of steps culminating in reduction with lithium aluminum hydride in ether. To enable its efficient implementation, a homogeneous reaction medium, a benzotrifluoride otherwise known as (trifluoromethyl)toluene, was employed.