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.^[1]

Illustrative is the synthesis of CB₉H₁₄⁻ from commercially available decaborane.^[2]

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

^ Russell N. Grimes (2016). Carboranes, 3rd Edition. Elsevier. ISBN 9780128019054.
^ Brellochs, Bernd; Bačkovský, Jaroslav; Štíbr, Bohumil; Jelínek, Tomáš; Holub, Josef; Bakardjiev, Mario; Hnyk, Drahomír; Hofmann, Mathias; Císarová, Ivana; Wrackmeyer, Berndt (2004). "New Ways to a Series of Parent Representatives of the Eight-, Nine-, and Ten-Vertex Monocarbaborane Family". European Journal of Inorganic Chemistry. 2004 (18): 3605–3611. doi:10.1002/ejic.200400125.

[1] Russell N. Grimes (2016). Carboranes, 3rd Edition. Elsevier. ISBN 9780128019054.

[2] Brellochs, Bernd; Bačkovský, Jaroslav; Štíbr, Bohumil; Jelínek, Tomáš; Holub, Josef; Bakardjiev, Mario; Hnyk, Drahomír; Hofmann, Mathias; Císarová, Ivana; Wrackmeyer, Berndt (2004). "New Ways to a Series of Parent Representatives of the Eight-, Nine-, and Ten-Vertex Monocarbaborane Family". European Journal of Inorganic Chemistry. 2004 (18): 3605–3611. doi:10.1002/ejic.200400125.

[1]

[2]