Oxa bowls: synthesis of new tetraoxa-cages and their C-H···O-mediated solid-state architecture

Abstract

We have envisioned a new family of oxa-bowls, and a general approach to these entities has been proposed through polycyclic frameworks having two converging olefinic double bonds. Ozonolysis of such molecules was envisaged to give all-cis-tetraaldehyde functionality, which could undergo intramolecular cascade acetalization to oxa-bowls having C_2v symmetry. Homohypostrophene 16a and its functionalized derivative 16b and hypostrophene 17 on ozonolysis furnished the oxa-cages 22a, 22b, and 23, respectively. Single-crystal X-ray analysis of 22a and 23 showed an interesting network of C-H···O interactions mainly involving the nonacidic cycloalkane hydrogen atoms. The molecule 22a exhibits an interesting tapelike C-H···O hydrogen bonding motif in its crystal structure. On the other hand, the molecule 23 revealed an undulated ribbonlike C-H···O motif. The "chain of rings" pattern of C-H···O interactions in 23 has been observed for the first time in the solid-state structure of oxa-bowls.