Organo-alkali Compounds.

Some Organic Reactions Involving the Occurence of Free Radicals in Solution.

“…but it is doubtful whether this same mechanism can be applied to the hydrocarbon syntheses of Fittig, Wurtz, and Ullmann, which are usually carried out in inert solvents: e.g., 2C2H6I + 2Na -> C2H5C2H6 + 2NaI 2C6H6I + 2Cu -> C6H6C6H6 + Cu2I2 since the reactions may proceed instead by means of the formation of organometallic compounds, e.g., C2H6Br + 2Na -> (C2H6)-Na+ + NaBr C2H6Na + BrC2H6 -> C2H6C2H6 + NaBr and evidence can be adduced in support of each theory (167,3,139,169,173,103).…”

The Chemical Behavior of the Organoalkali Compounds.

“…In a similar way 1,1,1 -triphenylethane (129), (CeH5)3CCH3, is not acidic enough to be affected by potassium amide in liquid ammonia. The activating influence is realized when the phenyl group is attached directly or through a vinyl system to the atom which holds the acidic hydrogen or acid-functioning group (128). When it is otherwise situated, the effect need not be the same.…”

“…Positions of compounds enclosed in brackets are estimated. Ammonia is placed above diphenylamine because of the observation of Wooster (128), that the hydrogen in a benzohydryl type compound was replaced by metal in reaction with potassium amide. If the position of ammonia is correct, the values for methane, ethane, and trimethylmethane may be considerably less than indicated.…”

Reactions of Solutions of Metals in Liquid Ammonia.

“…A few articles which have already appeared in this journal are closely related to certain portions of this review and may be consulted with profit in connection with it. The subjects of these articles are: (1) "The chemistry of the alkali amides" (18, 22); (2) "Metallic salts of alcohols and alcohol analogs" (73); and (3) "Organoalkali compounds" (388).…”