Abstract
The synthesis of several chiral tropocoronands based on 1,2-cyclohexanediamine (7) and 1,2-diphenylethylenediamine (8) has been accomplished. X-ray crystallography has confirmed the structure of two metallated derivatives, Cu(II)(TC-4,cyhex) (9) and Ni(II)(TC-4,cyhex) (10), that are indicative of the types of chiral complexes that can be formed from these systems.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 7341-7344 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 38 |
| Issue number | 42 |
| DOIs | |
| State | Published - Oct 20 1997 |
Bibliographical note
Funding Information:(+)-Ni(TC-4,cyhex) (10). IH NMR (CDC13, 500 MHz, assignments supported by 1H-1H COSY) 8 6.71 (dddd, J = ~10, -9.5, 3.5,1 Hz, 2H, NC=CH-CH), 6.68 (dddd, J = -10, -9.5, 4.0, 1.5 Hz, 2H, N'C=CH-CH), 6.24 (brd, J = 10.8 Hz, 2H, NC=CH), 6.18 (brd, J = 11.3 Hz, 2H, N'C=CH), 6.08 (dd, J = 9.3, 9.3 Hz, 2H, NC=CH-CH=CH), 3.73 (m, 2H, R2CHN), 3.25 (dddd, J = 13.9, -2, -2, -2 Hz, 2H, NCI~II-I'R),3 .15 (dd, J = 13.7, 9.6 Hz, 2H, NCHI-I'R), 2.69 (br d, J = 13.3 Hz, 2H, H3eq), 2.03 (m, 2H, NCH2CHH'R), 1.83 (m, 2H, NCH2CHH'R), 1.75 (m, 2H), 1.43 (m, 2H), and 1.25 (m, 2H, H3ax); IR (thin film) 2930, 1581, 1505, 1424, 1419, 1394, 1229, and 725 cm -I. HRMS (FAB) calcd for C24H2sNiN4 \[M+l\+] 431.1667, found 431.1725. Anal. Calcd for C24H28N4Ni: C, 66.85; H, 6.55, N, 12.99. Found: C, 66.94; H, 6.85, N, 12.72. Acknowledgment, This research was supported in part by the donors of the Petroleum Research Fund, administered by the American Chemical Society; Research Corporation; the University of Wisconsin--Eau Claire; and the National Institutes of Health. We thank Dr. Victor G. Young, Jr. (University of Minnesota) for the X-ray crystallographic analysis.