Quantitative syntheses of permethylated closo-1,10-R2C2B8Me8 (R = H, Me) carboranes. Egg-shaped hydrocarbons on the Frontier between inorganic and organic chemistry

Mario Bakardjiev; Oleg L Tok; Aleš Růžička; Zdeňka Růžičková; Josef Holub; Drahomír Hnyk; Jindřich Fanfrlík; Bohumil Štíbr

doi:10.1039/c8ra06640j

Quantitative syntheses of permethylated closo-1,10-R₂C₂B₈Me₈ (R = H, Me) carboranes. Egg-shaped hydrocarbons on the Frontier between inorganic and organic chemistry

RSC Adv. 2018 Nov 14;8(67):38238-38244. doi: 10.1039/c8ra06640j.

Authors

Mario Bakardjiev¹, Oleg L Tok¹, Aleš Růžička², Zdeňka Růžičková², Josef Holub¹, Drahomír Hnyk¹, Jindřich Fanfrlík³, Bohumil Štíbr¹

Affiliations

¹ Institute of Inorganic Chemistry, Academy of Sciences of the Czech Republic Husinec-Řež 1001 Czech Republic stibrb@seznam.cz.
² Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice Studentská 573 532 10 Pardubice Czech Republic.
³ Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo nám. 2, 166 10 Prague 6 Czech Republic.

Abstract

Electrophilic methylation of the closo-1,10-R₂C₂B₈H₈ (1) (R = H or Me) dicarbaboranes at higher temperatures or thermal rearrangement of the 1,6-R₂C₂B₈Me₈ (3) compounds at 400-500 °C generated the B-permethylated derivatives closo-1,10-R₂C₂B₈Me₈ (2) in quantitative (>95%) yields. The compounds exhibit extreme air stability as a consequence of a rigid, egg shaped hydrocarbon structures incorporating inner 1,10-C₂B₈ carborane core.