Sureshan, Kana M. ; Murakami, Tomohiro ; Miyasou, Tomomi ; Watanabe, Yutaka (2004) Topochemical Transketalization Reaction Driven by Hydrogen Bonding Journal of the American Chemical Society, 126 (30). pp. 9174-9175. ISSN 0002-7863
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Official URL: http://doi.org/10.1021/ja0483847
Related URL: http://dx.doi.org/10.1021/ja0483847
Abstract
An unusual thermal isomerization of 1,2;3,4-di-O-isopropylidene-myo-inositol to 1,2;5,6-di-O-isopropylidene-myo-inositol was observed in the solid state. A detailed study revealed that this ketal migration is a topochemically driven one. X-ray structure revealed that strong intermolecular hydrogen bonding in the crystal preorganizes the hydroxyl and ketal carbon in a transition-state-like arrangement favorable for the reaction. The 5-OH of each molecule faces the trans ketal carbon of a neighboring molecule at a close distance and an angle of approach near to linearity, making a trigonal-bipyramidal-like arrangement in the crystal, which could facilitate the reaction. This is the first report of a topochemical transketalization reaction.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 119849 |
| Deposited On: | 17 Jun 2021 12:41 |
| Last Modified: | 17 Jun 2021 12:41 |
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