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.;

Na/naphthalene in tetrahydrofuran byproducts: NaCl; under Ar; Ga-compd./THF added slowly to Na naphthalenide/THF at room temp. over 30 min, mixt. stirred; 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.;

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.;

in diethyl ether The Grignard soln. is added to a soln. of GaCl3 in Et2O over a period of 20 min. (under Ar), and stirred at room temp. for 18 h.; vacuum distn.; elem. anal.;

Na; C10H8 in tetrahydrofuran byproducts: NaCl, C10H10, C10H8; Ar-atmosphere; stirring (room temp., 5 d); evapn. (vac.), drying (dynamic vac., 24 h), extg. (pentane), recrystn. (-78°C); elem. anal.;

in hexane a soln. of freshly sublimed 1,4-(3,3-dimethyl-1-butynyl)benzene in n-hexane was treated with dineopentylgallium hydride, the mixt. was heated atreflux for 14 h, cooled to room temp.; concd., the solvent was removed in vac., the residue was evacuated (<1E-2 Torr) at 50°C for 3 h, recrystd. from toluene (20/-15°C); elem. anal.;

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

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

in hexane under Ar, 3 equiv. of Li-compd., reflux in n-hexane for 16 h;

in hexane under Ar atm. soln. R2GaH in hexane was treated with soln. bisalkyne in hexane at room temp. and heated under reflux for 15-20 h; soln. was cooled to room temp. and filtered, concd. in vacuo at room temp. and cooled to -80°C, Ga(CH2-t-Bu)3 was removed at 55°C (1E-3 Torr), recrystn. from n-hexane; elem. anal.;