One Step Syntheses of Heteropropellanes

References

• Grimme , W. , Kaufhold , M. , Dettmeier , V. and Vogel , E. 1966 . Angew. Chem. Int. Ed. Engl , 5 : 604
   Google Scholar
• Williams , J. R. and Ziffer , H. 1967 . J. Chem. Soc. Chem. Comm. , : 194
   Google Scholar
• Gargill , R. L. , Damewood , J. R. and Cooper , M. M. 1966 . J. Am. Chem. Soc. , 88 : 1330
   Google Scholar
• Weiss , U. and Edwards , J. M. 1968 . Tetrahedron Lett. , 47 : 4885
   Google Scholar
• Bloomfield , J. J. and Irelan , W. J. R. S. 1966 . J. Org. Chem. , 31 : 2017
   Google Scholar
• Altman , J. , Babad , E. , Itzchaki , J. and Ginsburg , B. 1966 . Tetrahedron , : 279
   Google Scholar
• Vogel , E. , Maier , W. and Eimer , J. 1966 . Tetrahedron Lett. , 6 : 655
   Google Scholar
• Aped , P. , Fuchs , B. , Goldberg , I. , Senderowitz , H. , Tartakovsky , E. and Weinman , S. 1992 . J. Am. Chem. Soc. , 114 : 5585
   Google Scholar
• Farfán , N. , Santillan , R. L. , Castillo , D. , Cruz , R. , Joseph-Nathan , P. and Daran , J. C. 1992 . Can. J. Chem. , 70 : 2664
   Web of Science ®Google Scholar
• Farfán , N. , Santillan , R. , Guzmán , J. B. , Castillo , B. , Ortíz , A. , Daran , J. C. , Robert , F. and Halut , S. 1994 . Tetrahedron , 50 : 9951
   Web of Science ®Google Scholar
• Ortíz , A. , Farfán , N. , Santillan , R. , Rosales , M. J. , García-Baéz , E. , Daran , J. C. and Halut , S. 1995 . Tetrahedron Asymmetry , 6 : 2715
   Google Scholar
• Compound 1: m.p. 144–146°C; 1H NMR (270 MHz, CDCl3) δ: 4.01 (1H, ddd, J=12, 11, 4 Hz, H-3ax), 3.74 (1H, dd, J=11, 4 Hz, H-3eq), 3.50 (1H, ddd, J=12, 11, 4 Hz, H-4ax), 2.50 (1H, dd, J=12, 4 Hz, H-4eq), 2.60 (1H, m, H-11ax), 1.50–1.80 (2H, m, H-12ax, eq) and 1.00–1.25 (1H, m, H-11eq) ppm; 13C NMR (67.8, MHz, CDCl3) δ: 84.0 (C-1), 62.6 (C-3), 39.1 (C-4), 32.7 (C-11) and 23.2(C-12) ppm; MS, m/z (%):198, (M+, 2), 167 (7), 154 (5), 139 (5), 112 (19), 98 (100), 85 (20), 55 (27), 36 (41); IR v max (KBr): 3302, 2956, 2928, 1636, 1082, 1034, 924, 830 cm−1
   Google Scholar
• Compound 2: m.p. 224–225°C; 1H NMR (270 MHz, DMSO-d6) δ: 7.05 (s, 1H, NH), 6.75–6.52 (4H, m, arom.) and 1.83–1.06 (4H, m, aliphat.) ppm; 13C NMR (67.80 MHz, DMSO-d6) δ: 141.0 (C-3), 129.8 (C-4), 120.7 (C-17), 118.3 (C-16), 115.6 (C-15), 114.0 (C-18), 81.8 (C-1), 32.6 (C-11) and 22.7 (C-12) ppm; MS, m/z (%), 294 (M+ 55), 265 (2), 237 (1), 187 (100), 158 (18), 146 (17), 120 (7), 93 (9), 65 (12), 28 (88); IR v max (KBr): 3334, 2926, 1608, 1502, 1274, 1236, 1006, 944, 870 cm−1
   Google Scholar
• Crystal data: Colorless cubic crystals of compound 1, C10H18N2O2 (M=198.26 gmol−1), crystallized in the monoclinic space group C 2/c, crystal dimensions 0.3 x 0.4 x 0.5 mm,3 a=12.740(1), b=7.349(1), c=11.366(1) Å, β=109.943(3)°, V=1000.52(6) Å,3 by least squares refinement on diffractometer angles for 24 automatically centered reflections, Z=4, ρcalcd=1.31 Mgm,−3 μ=0.09 mm.−1 A total of 1253 reflections was measured, of which 1088 were independent and of these 662 were considered observed [F>3σ(F)], absorption correction: DIFABS (min: 0.65, max: 1.20), corrections were made for Lorentz and polarization effects. Solution and refinement: direct methods (SHELXS-86) for structure solution. Nonhydrogen atoms were refined anisotropically, hydrogen atoms were found by difference Fourier rmaps and refined with an overall isotropic thermal parameter (CRYSTALS, Program for Refinement of Crystal Structures, D.J. Watkin, J.R Caruthers, P.V. Betteridge, Univ. Oxford, version 9, 1994). R=0.047, Rw=0.045 from 662 reflections with F>3σ(F) for 92 variables against /F/, w=1.0, s=2.69. Largest residual electron density peak/ hole in the final difference map: ρmax=0.26, ρmin= −0.20 e-/Å3
   Google Scholar
• Kirby , A. J. 1983 . “The anomeric effect and related stereoelectronic effects at oxygen,” , 77 Berlin : Springer Verlag .
   Google Scholar
• Farfán , N. , Santillan , R. , Castillo , B. , Carretero , P. , Rosales , M. de J. , García-Baez , E. , Flores-Vela , A. , Daran , J. C. and Halut , S. 1994 . J. Chem. Res. (M) , : 458 (S), 1994, 2521
   Google Scholar