ortho-Carborane

The organic substituents are removed by ester hydrolysis followed by oxidation:[2] Upon heating to 420 °C, it rearranges to form the meta isomer.

Dicarbollides, being strong electron donors, stabilize higher oxidation states, e.g. Ni(IV).

The CH vertices of closo-dicarbadodecaboranes undergo deprotonation upon treatment with organolithium reagents:[9] These dilithiated compounds react with a variety of electrophiles, e.g. chlorophosphines, chlorosilanes, and sulfur.

[10] Many of the same compounds can be produced by hydroboration of alkynes: ortho-Carborane can be converted to highly reactive carborynes with the formula B10C2H10.

[14] Iodinated derivatives of carborane can be further modified to access boron alkylated products via a cross coupling reaction.

This can be done by treating the halogenated carborane with a Grignard reagent in the presence of a phosphine palladium complex.

The reaction mixture is allowed to stir at room temperature for two days, forming a copper-metalated carborane cage.

The crude product is then purified via column chromatography and affords one half-equivalent of the carbon-carbon linked dimer of the original ortho-carborane in high yields.

o-dicarborane and its meta- and para-isomers (CH vertex indicated with black spheres).
Diiodination of ortho-carborane at the 9 and 12 vertices.
Alkylation of ortho-carborane at the 9 and 12 vertices via cross-coupling reaction with a palladium catalyst.
Copper-mediated coupling of two ortho-carborane cages.