Aryl magnesium bromides were treated with N, N-dimethylformamide dimethylacetal (DMFDA) in tetrahydrofuran to obtain the corresponding 1, 1-diaryltrimethylamines. 2ArMgBr+CH3_??_CH3_??_N-CH_??_OCH3_??_OCH3→CH3_??_CH3_??_N-CH_??_Ar_??_Ar Ar = C6H5, p-CF3OC6H4, o-CH3OC6H4, p-CH3C6H4, m-CH3C6H4, o-CH3C6H4 N'-Arylarylamidines reacted with an exess amount of DMFDA to afford the corresponding N-dimethylaminomethylideneamidines, as follows : ArC_??_NH2_??_NAr'+CH3_??_CH3_??_N-CH_??_OCH3_??_OCH3→ArC_??_N=CH-N_??_CH3_??_CH3_??_NAr' Ar =p-CH3C6H4 Ar' C6H5, Ar C6H5 Ar' C6H5, Ar = 2-C10H7 Ar' = C6H5, Ar =p-ClC6H4 Ar' = C6H5, Ar C6H5 Ar' =p-ClC6H4 Condensation reactions of o-aminobenzamide and o-aminobenzenesulfamide with DMFDA or ethyl orthoformate yielded 4-keto-3, 4-dihydroquinazoline and 2H-1, 2, 4-benzothiadiazine 1, 1-dioxide, respectively.
The Friedel-Crafts self-condensation of benzyl chloride has been chosen as a means to evaluate the catalytic activities of about 50 kinds of metal halides. The lowest temperature required for initiating the reaction served as an index for the activity. The order of the activities was in agreement with that found in the ordinary Friedel-Crafts reactions. The results are discussed in the light of the electrosolution voltage and electro-negativity of metal halides.