Terminally dimetallated N,N '-dimethylpiperazines with doubly spirocyclic structures

Tian X, Fröhlich R, Mitzel NW (2006)
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE 632(2): 307-312.

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Abstract
Dilithiated N,N'-dimethyl-piperazine, LiCH2N(CH2CH2)(2) NCH2Li (2) was prepared by transmetallation of N,N'-bis(trimethylstannylmethyl)-piperazine (1) with (BuLi)-Bu-n and was isolated as a highly pyrophoric yellowish powder in high yield. Compound 2 was characterized by elemental analysis and was reacted as difunctional aminomethylating reagent with dialkyl-earth metal chlorides, R2MCl (M=Al, Ga; R=Me, Bu-t) which resulted in the formation of spirocyclic adducts of N,N'-bis(dialkylmetallamethyl)-piperazine and unreacted dialkylmetal chlorides, [(Me2AlCl)Me2-AlCH2N(CH2CH2)(2)NCH2AlMe2(ClAlMe2)] (3) and [((Bu2GaCl)-Bu-t)t-Bu2GaCH2N(CH2CH2)(2)(NCH2GaBu2)-Bu-t((ClGaBu2)-Bu-t)] (4) with five-membered rings. Compounds 1, 3 and 4 were identified by NMR-spectroscopy (H-1, C-13, Sn-119 for 1, Al-27 for 3), mass spectra (EI, for 1) and by crystal structure determinations.
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Tian X, Fröhlich R, Mitzel NW. Terminally dimetallated N,N '-dimethylpiperazines with doubly spirocyclic structures. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE. 2006;632(2):307-312.
Tian, X., Fröhlich, R., & Mitzel, N. W. (2006). Terminally dimetallated N,N '-dimethylpiperazines with doubly spirocyclic structures. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 632(2), 307-312.
Tian, X., Fröhlich, R., and Mitzel, N. W. (2006). Terminally dimetallated N,N '-dimethylpiperazines with doubly spirocyclic structures. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE 632, 307-312.
Tian, X., Fröhlich, R., & Mitzel, N.W., 2006. Terminally dimetallated N,N '-dimethylpiperazines with doubly spirocyclic structures. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 632(2), p 307-312.
X. Tian, R. Fröhlich, and N.W. Mitzel, “Terminally dimetallated N,N '-dimethylpiperazines with doubly spirocyclic structures”, ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, vol. 632, 2006, pp. 307-312.
Tian, X., Fröhlich, R., Mitzel, N.W.: Terminally dimetallated N,N '-dimethylpiperazines with doubly spirocyclic structures. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE. 632, 307-312 (2006).
Tian, X, Fröhlich, R, and Mitzel, Norbert W. “Terminally dimetallated N,N '-dimethylpiperazines with doubly spirocyclic structures”. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE 632.2 (2006): 307-312.
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