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2 Unlike the reaction between biacetyl and 1,3-propanediamine to form 2,3,9,10-Me4[14] 1,3,8,10-tetraene-1,4,8,1 l-N4 (Sec. 4), the condensation of biacetyl with N,N'bis(3-aminopropy1)ethylenediamine is particularly sensitive t o excess acetate so that the procedures given use the optimized conditions. A. HC1 + CH,-C-C-CH, II II ZnC1, HCl 0 0 [Ni(Me, [14] -1,3-dieneN4][ZnC14] + 6 H 2 0 + 2CH3COOH *Department of Chemistry, The Ohio State University, Columbus, OH 43210. 33 mole) of concentrated hydrochloric acid.

D. Thesis, The Ohio State University, 1969. 4. S. C. Jackels, K. Farmery, E. K. Barefield, N. J. Rose, and D. H. Busch, Inorg. , 11, 2893 (1972). 5 . C. R. D. Thesis, The Ohio State University, 1971. 6. K. Farmery and D. H. Busch, Chem. , 1970, 1041. 7. K. Farmery and D. H. Busch,Inorg. ). 8. A. M. Tait and D. H. Busch, Inorg. , 16, 966 (1977). Inorganic Syntheses, Volumem I I 1 Edited by Bodie E. Douglas Copyright © 1978 by John Wiley & Sons, Inc. 5. -dieneN, Complexes 21 5. 2,3-DIMETHYL-174,8,1 1 -TETRAAZACYCLOTETRADECA173-DIENE(2,3-Me2[ 141 -1,3-diene-1,4,8,11-N4)COMPLEXES Submitted by A.

6. J. C. Dabrowiak, F. V. Lovecchio, V. L. Goedken, and D. H. Busch, J. Am. Chem. , 94,5502 (1972). 7. R. A. D. Wentworth and T. S . , 4, 709 (1965). 3. 11- HEPTADECA-1(17),2,11,13,15PENTAENE (2,6-Me214]-1,3,6-triene-1,4,7,1 l-N4) COMPLEXES 2’,6’:3,5-Pyo[ Submitted by A. MARTIN TAIT* and DARYLE H. BUSCH* Checked by J. WILSHIRE’ and A. B. P. LEVER? ’ As is often the case with Schiff-base condensations of the type, the addition of a small amount of acid catalyzes the reaction. 2-4 *Department of Chemistry The Ohio State University, Columbus, OH 43210.

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