Amylsodiurn dimetalates benzene chiefly in the meta position but the ratio of meta to para can be altered by the alkoxide t-Butylphenoxide is attacked which is associated with the reagent. in the 2,6-position.Thiophene is easily dimetalated in the 2,5-positions. Isopropylbenzene and sec-butylbenzene are dimetalated in the 3,5-positions.

IKTRODUCTIONThis work was intended to be a study of the metalation of the benzene nucleus under the directing influence of an alkyl group which couId not itself be metalated, but steric factors probably limit the scope of polar influence. KO ortho metalation occurs. Only one dimetalation, the m,m', can take place because of the hindrance at the two ortho positions and the failure of sodium to attack a position adjacent to another sodium ion on the ring. Nevertheless some excellent demonstrations of the effects of associated salts, which is one of the special aspects of the work in this laboratory, have been achieved.

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