SYNTHESIS AND CHARACTERIZATION OF A NOVEL PENTACYCLIC C-16 DIKETONE AND DERIVATIVES

The syntheses and crystal structures of pentacyclo[9.4. 1.0(5,14).0(7,13).0(12.15)]hexadecane-3,9-dione (2), a novel C-16 diketone with potential inclusion ability, and the products of the reaction of 2 with n-butyllithium and meso-erythritol (i.e., meso-1,2,3,4-butanetetrol) are described. Crystal data: 2.H2O, orthorhombic, Pmmn, a = 10.7385(8), b = 9.0188(6), c = 6.8411(4) angstrom, V = 662.55(7) angstrom3, and R = 0.039 (379 reflections); 3 (product from reaction with n-butyllithium), triclinic, P1BAR, a = 8.7192(7), b = 10.9351(8), c = 12.1842(8) angstrom, alpha = 68.933(5), beta = 75.850(6), gamma = 80.309(6)-degrees, V = 1047.0(1) angstrom3, and R = 0.081 (1811 reflections); 4 (product from reaction with erythritol), triclinic, P1BAR, a = 7.7224(8), b = 10. 1976(8), c = 10.7021(9) angstrom, alpha = 85.405(7), beta = 85.766(8), gamma = 76.056(7)-degrees, V = 814.0(1) angstrom3 , and R = 0.052 (1471 reflections).