SYNTHESIS AND CHARACTERIZATION OF UNUSUAL TETRAAMINOALKENES (ENETETRAMINES)

Two general routes are described for the synthesis of the title compounds from the reaction of either (A) the dimethyl acetal of N,N-dimethylformamide and an appropriate N,N'-bis(secondary amine), or (B) sodium hydride and a 4,5-dihydroimidazolium or tetrahydropyrimidinium salt. The following new compounds have been made: trans-RN(CH2)2N(R')C = CN(R')(CH2)2NR [R = Et and R' = Me (1a) or CH2Ph (1b)] and [GRAPHICS] m = 2, and R = CH2Ph (3); or n = 2, m = 3, and R = CH2Ph (4)]. X-Ray data on crystalline [CN(R)(CH2)2NR]2 (R = CH2Ph) and (2b) [data in parentheses] show a short C = C bond, 1.319(8) angstrom [1.329(5) angstrom], long C(sp2)-N bonds, av. 1.437(11) angstrom [1.424(4) angstrom], with each of the four nitrogen atoms in a pyramidal sp3 environment.