H. Schumann, Katharina Kuse, S. Dechert
2004
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Zeitschrift für Naturforschung. B, A journal of chemical sciences
Abstract
1,5-Bis(methylsulfonyloxi)-3-aza-3-p-toluenesulfonylamidopentane (1) reacts with 4-benzyl-1,7-bis(p-toluenesulfonyl)diethylenetriamine (2) and 4-benzyl-1,7-bis(p-nitrophenylsulfonyl)diethylenetriamine (3) and Cs 2 CO 3 yielding 1-benzyl-4,7,10-tris(p-toluenesulfonyl)-1,4,7,10-tetraazacyclododecane (9a) and 1-benzyl-4,10-bis(p-nitrophenylsulfonyl)-7-p-toluenesulfonyl)-1,4,7,10-tetraazacyclododecane (10a), respectively. The corresponding dimers 1,13-bis(benzyl)-4,7,10,16,19,22-hexa(p-toluenesulfonyl)-1,4,7,10,13,16,19,22-octaazacyclotetracosane (9b) and 1,13-bis(benzyl)-4,10,16,22-tetra(p-nitrophenylsulfonyl)-7,19-bis(p-toluenesulfonyl)-1,4,7,10,13,16,19,22-octaazacyclotetracosane (lOb) could not be isolated but detected by mass spectroscopy. The reactions of 1 with 4-heptyl-1,7-bis(p-nitrophenylsulfonyl)diethylenetriamine (5) and Cs 2 CO 3 results in the formation of 1-heptyl-4,10-bis(p-nitrophenylsulfonyl)-7-p-toluenesulfonyl)-1,4,7,10-tetraazacyclododecane (11) and 1 reacts with 4-benzyl-diethylenetriamine (4) and Cu(O 2 CCH 3 ) 2 forming the dimeric copper complex [{C 6 H 5 CH 2 N(CH 2 CH 2 NH 2 } 2 Cu(μ-Cl)OSO 2 CH 3 ] 2 (12). The 1 H and 1 3 C NMR spectra of the new compounds as well as the single crystal X-ray structure analyses of 9a, 11, and 12 are reported and discussed.