in pentane Both compounds are dissolved in pentane and transferred into a side-arm flask. The flask is cooled to -196°C, evacuated and then stirred for 18 h at room temp.; filtn., removal of pentane by vacuum distn., recrystn. from pentane at -78°C or vacuum distn.; elem. anal.;

1: Na/naphthalene / tetrahydrofuran 2: HCl / tetrahydrofuran View Scheme

Li/naphthalene in tetrahydrofuran byproducts: LiCl; under Ar; react. of Ga-compd./THF with Li/C10H8 in THF at -78°C,mixt. slowly warmed to room temp., mixt. turned dark reddish-brown, soln. stirred (18 h); THF removed (rapid vacuum distn.), mixt. subjected to dynamic vac. (24 h), volatile materials trapped (Ga(CH3CMe3)3 and C10H8); non-volatile residue extd. (pentane), filtered, evapn., elem. anal.;

1: Na/naphthalene / tetrahydrofuran 2: HCl / tetrahydrofuran 3: Na/naphthalene / tetrahydrofuran View Scheme