Adaptation of the Barton Reaction to Carborane Chemistry: The Synthesis and Reactivity of 2-Hydroxyimino-1-hydroxymethylnona-B-methyl-1,12-dicarba-closo-dodecaborane(12).

Just one of the ten methyl groups of deca-B-methyl-1,12-dicarba-closo-dodecarborane(12) (1) is selectively functionalized in a reaction sequence in which photolysis of a nitrite of 1 is the key step. Reduction of the resulting aldoxime with LiAlH4 generates, by way of the first Beckmann rearrangement of a boron-substituted oxime, the methylamino alcohol 2. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.