Oxa-bowls: formation of exceptionally stable diozonides with novel, C–H···O hydrogen bond directed, solid state architecture

Abstract

Several tetraquinane-based diolefins on ozonization furnish unusually stable diozonides of ‘bowl-like’ topology and their solid state structure reveals interesting architecture woven through a network of unique C–H···O interactions.

References

1. G. Mehta and R. Vidya, Tetrahedron Lett., 1997, 38, 4173; G. Mehta and R. Vidya, Tetrahedron Lett., 1997, 38, 4177.
2. R. Taylor and O. Kennard, J. Am. Chem. Soc., 1982, 104, 5063; G. R. Desiraju, Acc. Chem. Res., 1996, 29, 441; T. Steiner, Chem. Commun., 1997, 727.
3. (a) K. J. McCullough, S. Tanaka, K. Teshima and M. Nojima, Tetrahedron, 1994, 50, 7625; (b) H. N. Junker, W. Schafer and H. Niedenbruck, Chem. Ber., 1967, 100, 2508; (c) H. Mayr, J. Baran, E. Will, H. Yamakoshi, K. Teshima and M. Nojima, J. Org. Chem., 1994, 59, 8126; (d) J. S. Buckleton, G. R. Clark and C. E. F. Rickard, Acta Crystallogr., Sect. C, 1995, 51, 494.
4. G. Mehta, A. Srikrishna, A. V. Reddy and M. S. Nair, Tetrahedron, 1981, 37, 4543; G. Mehta and M. S. Nair, J. Am. Chem. Soc., 1985, 107, 7519; G. Mehta and K. Raja Reddy, J. Org. Chem., 1987, 52, 460; G. Mehta and K. Raja Reddy, Tetrahedron Lett., 1988, 29, 3607.
5. All compounds were fully characterized on the basis of their spectral and analytical data.
6. G. M. Sheldrick, SHELXL-97, University of Göttingen, Germany, 1997.