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Brellochs reaction

In organoboron chemistry, the Brellochs reaction provides a way to generate the monocarboranes. The Brellochs method uses formaldehyde to insert single carbon atoms into boron hydrides.

Illustrative is the synthesis of CB<sub>9</sub>H<sub>14</sub><sup>−</sup> from commercially available decaborane.

B<sub>10</sub>H<sub>14</sub> + CH<sub>2</sub>O + 2 OH<sup>−</sup> + H<sub>2</sub>O → CB<sub>9</sub>H<sub>14</sub><sup>−</sup> + B(OH)<sub>4</sub><sup>−</sup> + H<sub>2</sub>

Oxidation of the arachno anion gives nido-6-CB<sub>9</sub>H<sub>12</sub><sup>−</sup>. Base degradation of the latter gives arachno-4-CB<sub>8</sub>H<sub>14</sub>.

References