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The fact that many of the colored organo-alkali compounds conduct the electric current in ether and in liquid ammonia solution,3 and behave in other ways as salts, implies that the corresponding hydrides should exhibit an acidic character, albeit an exceedingly weak one. In fact, it has been shown that they may react with the ammono-base, potassium amide, in liquid ammonia solution to form the potassium salts. Thus triphenylmethane forms potassium triphenylmethide4and potassium benzhydrolate yields dipotassium benzophenone6 (CeHshCHOK + KNH2 -> (C6H5)3CKOK + NH"(2)This behavior indicates that these hydrides are ionized to a greater degree than the solvent ammonia, for otherwise reaction would be expected to proceed in the opposite direction corresponding to an ammonolysis of the salts. In the case of the alkali alkyls and alkali phenyls8 such an ammonolysis does occur, demonstrating that the corresponding hydrocarbons are ionized to a less degree than ammonia.7 Accordingly it is impossible to obtain organo-alkali compounds by the action of potassium amide upon these hydrocarbons.

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REDUCTION OF NAPHTHALENE BY ALKALI METALS 179 I desire to express my hearty thanks to Professor Hata for the interest which he has kindly taken in this work.Summary 5-Acetamino-6-hydroxy-, 5-acetamino-8-hydroxy-, 7-iodo-5-acetamino-&hydroxy-and 7-acetamino-5-methyl-8-hydroxyquinoline have been prepared and characterized.The reaction between sodium and naphthalene in liquid ammonia solution was first investigated by Lebeau and Picon2 and the products which they obtained a t 15' were sodium amide and tetrahydronaphthalene. These facts are equally open to two different interpretations.It may be assumed that the naphthalene was reduced by nascent hydrogen generated by a reaction between the alkali metal and the solvent. 4Na + 4 " s -+-4NaNHe + 4(H) 4(H) + CioHs --f CioHirThis hypothesis is analogous to that advanced by Kekule, Kolbe, von Baeyer and others3 to explain reductions of organic substances with sodium amalgam and water.The formation of tetrahydronaphthalene may also be attributed to a solvolytic action of the solvent upon an organo-alkali compound which was formed as an intermediate product. I.(1)( 2 ) 11.This assumption is analogous to an alternative theory of amalgam reduction recently proposed by Willstatter, Seitz and B~m m .~ This reaction, therefore, is of especial interest a{a test case for indicating the possibilities of wider application of the two general hypotheses.Dipotassium6 and dilithium6 derivatives of naphthalene have been pre-

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