42568-27-4Relevant academic research and scientific papers
Practical synthesis of 1,12-difunctionalized o-carborane for the investigation of polar liquid crystals
Jankowiak, Aleksandra,Kaszynski, Piotr
, p. 8762 - 8769 (2014)
Two isomerically pure 1,12-difunctionalized derivatives of o-carborane, 12-iodo-1-vinyl (1b) and 12-iodo-1-phenyl (1c), are conveniently obtained on a practical scale in yields of 22% and 32%, respectively, by monoiodination of the corresponding o-carborane derivatives (4b and 4c) followed by separation of the regioisomers by crystallization (1b) and chromatography (1c). Subsequent functional group transformations gave access to other derivatives, including two liquid-crystalline compounds, in which o-carborane is a linear structural element. Regioselectivity of substitution on the carborane cage and on the benzene ring correlates with the inductive effect parameter of the substituent. The preparation of analogous derivatives of m-carborane was also investigated.
