Synthesis of some functional derivatives of o- and m-carboranes

Amides, amines, and alcohols were synthesized from 9-o- and 9-m-carboranecarboxylic chlorides. It follows from comparison of the H-1 NMR spectra of N,N-dimethyl-1-o- and -1-m-carboranecarboxamides and N,N-dimethyl-9-o- and -9-m-carboranecarboxamides that pi-bonding of the carborane polyhedron with the carbonyl group in 1-carboranyl dimethylamides is stronger than that in 9-carboranyl diethylamides. Oxidation of 9-hydroxymethyl-m-carborane with pyridinium chlorochromate gives 9-m-carboranylmethyl 9-m-carboranecarboxylate.