organoboron chemistry Organoborane or organoboron compounds are chemical compounds of boron and carbon that are organic derivatives of BH3, for example trialkyl boranes. Organoboron chemistry or organoborane chemistry is the chemistry of these compounds. Organoboron ...

, the Brellochs reaction proviides a way to generate the mono

carborane Carboranes are electron-delocalized (non-classically bonded) clusters composed of boron, carbon and hydrogen atoms.Grimes, R. N., ''Carboranes 3rd Ed.'', Elsevier, Amsterdam and New York (2016), . Like many of the related boron hydrides, these cl ...

s. The use of acetylenes to insert ''two'' carbons into boron hydrides is well established. The Brellochs method uses formaldehyde to insert single carbon atoms into boron hydrides. Illustrative is the synthesis of CB₉H₁₄⁻ from commercially available

decaborane Decaborane, also called decaborane(14), is the borane with the chemical formula B10 H14. This white crystalline compound is one of the principal boron hydride clusters, both as a reference structure and as a precursor to other boron hydrides. It ...

.{{cite journal , doi=10.1002/ejic.200400125, title=New Ways to a Series of Parent Representatives of the Eight-, Nine-, and Ten-Vertex Monocarbaborane Family, year=2004, last1=Brellochs, first1=Bernd, last2=Bačkovský, first2=Jaroslav, last3=Štíbr, first3=Bohumil, last4=Jelínek, first4=Tomáš, last5=Holub, first5=Josef, last6=Bakardjiev, first6=Mario, last7=Hnyk, first7=Drahomír, last8=Hofmann, first8=Mathias, last9=Císarová, first9=Ivana, last10=Wrackmeyer, first10=Berndt, journal=European Journal of Inorganic Chemistry, volume=2004, issue=18, pages=3605–3611 :B₁₀H₁₄ + CH₂O + 2 OH⁻ + H₂O → CB₉H₁₄⁻ + B(OH)₄⁻ + H₂ Oxidation of the arachno anion gives nido-6-CB₉H₁₂⁻. Base degradation of the latter gives arachno-4-CB₈H₁₄.

References

Organoboron compounds Cluster chemistry