SYNTHESIS OF 1,4,7,10-TETRA-N-ALKYL-1,4,7,10-TETRAAZA-CYCLODODECANES

REFERENCES

• For a recent review, see: Bernhardt , P.V. and Lawrance , G.A. 1990 . Coord. Chem. Rev. , 104 : 297 – 343 .
   Web of Science ®Google Scholar
• Aime , S. , Botta , M. , Fasano , M. and Terreno , E. 1998 . Chem. Soc. Rev. , 27 : 19 – 29 .
   Web of Science ®Google Scholar
• Reichert , E. , Anderson , J. and Welch , J. 1998 . Chem. Ind. , : 730 – 733 .
   Web of Science ®Google Scholar
• Dickins , R. , Gunnlaugsson , T. , Parker , D. and Peacock , R. 1998 . Chem. Commun. , : 1643 – 1644 .
   Web of Science ®Google Scholar
• Bruce , J. , Dickins , R. , Govenlock , L. , Gunnlaugsson , T. , Lopinski , S. , Lowe , M. , Parker , D. , Peacock , R. , Perry , J. , Aime , S. and Botta , M. 2000 . J. Am. Chem. Soc. , 122 : 9674 – 9684 .
   Web of Science ®Google Scholar
• Shionoya , M. , Kimura , E. and Shiro , M. 1993 . J. Am. Chem. Soc. , 115 : 6730 – 6737 .
   Web of Science ®Google Scholar
• Shinoya , M. , Sugiyama , M. and Kimura , E. 1994 . Chem. Commun. , : 1747 – 1748 .
   Web of Science ®Google Scholar
• Kimura , E. , Ikeda , T. and Shionoya , M. 1997 . Pure & Appl. Chem. , 69 : 2187 – 2195 .
   Web of Science ®Google Scholar
• Kimura , E. , Ikeda , T. , Aoki , S. and Shionoya , M. 1998 . J. Biol. Inorg. Chem. , 3 : 259 – 267 .
   Web of Science ®Google Scholar
• Koike , T. , Takamura , M. and Kimura , E. 1994 . J. Am. Chem. Soc. , 116 : 8443 – 8449 .
   Web of Science ®Google Scholar
• Coates , H. , Hadi , A. and Lincoln , F. 1982 . Aust. J. Chem. , 35 : 903 – 909 .
   Web of Science ®Google Scholar
• For the synthesis of 1,4,7,10-tetramethyl-1,4,7,10-tetraaza-cyclododecan by methylation of 1 using formic acid and formaldehyde, see: Barefield, E.K.; Wagner, F. Inorg. Chem. 1973, 12, 2435–2439. A alternative general strategy to introduce alkyl groups into cyclen is the acylation followed by reduction to the amine. Problems in this strategy are the incomplete reaction to amides with sterically demanding reagents or fatty acids and the formation of stable complexes with boron in the reduction step
   Google Scholar
• Hansen , G.R. and Burg , T.E. 1968 . J. Heterocycl. Chem. , 5 : 305
   Web of Science ®Google Scholar
• Aoki , S. , Honda , Y. and Kimura , E. 1998 . J. Am. Chem. Soc. , 120 : 10018 – 10026 .
   Web of Science ®Google Scholar
• For reports of a fourfold alkylation of cyclen, see: Gyr , T. , Mäcke , H.R. and Hennig , M. 1997 . Angew. Chem. , 109 : 2869 – 2871 . Angew. Chem., Int. Ed. Eng. 1997, 36, 2786–2788
   Google Scholar
• Stephens , K.W. and Lincoln , F. 1993 . J. Chem. Soc. Dalton Trans. , : 2123 – 2126 .
   Google Scholar
• de Martino Norante , G. , Di Vaira , M. , Mani , F. , Mazzi , S. and Stoppioni , P. 1990 . J. Chem. Soc., Chem. Commun. , : 438 – 439 .
   Google Scholar
• Di Vaira , M. , Mani , F. and Stoppioni , P. 1989 . J. Chem. Soc., Chem. Commun. , : 126 – 127 .
   Google Scholar
• Barefield , E.K. , Foster , K.A. , Freeman , G.M. and Hodges , K.D. 1986 . Inorg. Chem. , 25 : 4663 – 4668 .
   Web of Science ®Google Scholar
• 13C NMR spectra of all three compounds 2, 3, and 4 are well resolved and show one resonance signal for cyclen ring carbons
   Google Scholar
• Kalligeros , G.A. and Blinn , E.L. 1972 . Inorg. Chem. , 11 : 1145 – 1148 . For the synthesis of the nickel(II) complex of 1,4,7,10-tetrabenzyl-1,4,7,10-tetraaza-cyclododecane, see:
   Web of Science ®Google Scholar
• Styka , M.C. , Smierciak , R.C. , Blinn , E.L. , de Simone , R.E. and Passariello , J.V. 1978 . Inorg. Chem. , 17 : 82 – 86 . For the synthesis of the copper(II) complex of 1,4,7,10-tetrabenzyl-1,4,7,10-tetraaza-cyclododecane, see:
   Web of Science ®Google Scholar
• Sarther , C.M. and Blinn , E.L. 1976 . Inorg. Chem. , 15 : 3083 – 3087 . For the synthesis of the cobalt(II) complex 1,4,7,10-tetrabenzyl-1,4,7,10-tetraaza-cyclododecane, see:
   Web of Science ®Google Scholar
• This purity is sufficient for most application of such Lewis-acids. Further purification is possible, but requires RP HPLC separation or ion exchange chromatography
   Google Scholar
• Collman , J.P. and Schneider , P.W. 1966 . Inorg. Chem. , 5 : 1380 – 1384 . For the synthesis of a cobalt(III) complex of cyclen (1), see:
   Web of Science ®Google Scholar
• Cobalt(III) complexes require in general a coordination number of six, while cobalt complexes of tetrasubstituted cyclen ligands have a coordination number of five
   Google Scholar
• Coates , J.H. , Hadi , D.A. , Lincoln , S.F. , Dodgen , H.W. and Hunt , J.P. 1981 . Inorg. Chem. , 20 : 707 – 711 . Nickel(II) complexes of tetrasubstituted cyclen ligands prefer coordination numbers of four or five, whereas the parent system 1 yields Ni(II) complexes with coordination number six:
   Web of Science ®Google Scholar
• Kong , D.-Y. , Meng , L.-H. , Ding , J. , Xie , Y.-Y. and Huang , X.-Y. 2000 . Polyhedron , 19 : 217 – 223 .
   Web of Science ®Google Scholar
• Shionoya , M. , Kimura , E. and Shiro , M. 1993 . J. Am. Chem. Soc. , 115 : 6730 – 6737 .
   Web of Science ®Google Scholar
• Visser , H.C. , Reinhoudt , D.N. and de Jong , F. 1994 . Chem. Soc. Rev. , : 75 – 81 . o-NPOE: ortho-Nitrophenyloctylether. Used as solvent for carrier compounds in supported liquid membranes:
   Web of Science ®Google Scholar
• Tsukube , H. 1983 . J. Chem. Soc., Perkin Trans. 1 , : 29 – 34 .
   Google Scholar