C. Vinas et al., DIMETHOXYETHANE AS A SOLVENT FOR THE SYNTHESIS OF C-MONOSUBSTITUTED O-CARBORANE DERIVATIVES, Inorganic chemistry, 34(14), 1995, pp. 3844-3845
Dimethoxyethane is a reliable solvent for the synthesis of monosubstit
uted derivatives of o-carborane. The reaction of o-carborane with 1 eq
uiv of BuLi and the appropriate electrophile in dimethoxyethane yields
the desired monosubstituted derivative. The 1,2-Li-2-1,2-C2B10H10 com
pound is most probably avoided due to the bulkiness of the first Li(di
methoxyethane) substituent (see diagram), blocking attack by a second
Li(dimethoxyethane) group. The method encounters problems if C,C' ther
modynamically stable rings can be formed.