Cooperative effect of carborane and pyridine in the reaction of carboranyl alcohols with thionyl chloride: halogenation versus oxidation

Vincent Terrasson; José G Planas; Damien Prim; Clara Viñas; Francesc Teixidor; Mark E Light; Michael B Hursthouse

doi:10.1021/jo801672f

Cooperative effect of carborane and pyridine in the reaction of carboranyl alcohols with thionyl chloride: halogenation versus oxidation

J Org Chem. 2008 Nov 21;73(22):9140-3. doi: 10.1021/jo801672f. Epub 2008 Oct 28.

Authors

Vincent Terrasson¹, José G Planas, Damien Prim, Clara Viñas, Francesc Teixidor, Mark E Light, Michael B Hursthouse

Affiliation

¹ Institut Lavoisier de Versailles-UMR CNRS 8180, Université de Versailles-Saint-Quentin-en-Yvelines, 45 avenue des Etats-Unis, 78035 Versailles, France.

PMID: 18954110
DOI: 10.1021/jo801672f

Abstract

Thionyl chloride (SOCl2) acts as halogenation reagent in its reaction with 1-[phenyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaborane 1a, b but unexpectedly behaves as an oxidant for 1-[2'-pyridyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaboranes 2a, b. The synthesis and characterization of all new compounds, including structure determinations of 1a, 2a, 1-[phenyl(chloro)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane 3a, and 1-[2'-pyridyl(oxo)methyl]-2-methyl-1,2-dicarba-closo-dodecaboranes 4a are reported and the possible pathways are discussed.