Oxa Bowls: Synthesis of New Tetraoxa-Cages and Their C-H...O-Mediated Solid-State Architecture

Mehta, Goverdhan and Vidya, Ramdas (2000) Oxa Bowls: Synthesis of New Tetraoxa-Cages and Their C-H...O-Mediated Solid-State Architecture. In: Journal of Organic Chemistry, 65 (11). pp. 3497-3502.

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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 $C_2_v$ 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.

Item Type:	Journal Article
Publication:	Journal of Organic Chemistry
Publisher:	American Chemical Society
Additional Information:	Copyright for this article belongs to American Chemical Society.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	24 Jan 2005
Last Modified:	19 Jan 2012 06:47
URI:	http://eprints.iisc.ac.in/id/eprint/2697

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