Yadav, Veejendra ; Fallis, Alex G. (1991) Free-radical based cycloalkanol synthesis and annulation from thioacetal precursors Canadian Journal of Chemistry, 69 (5). pp. 779-789. ISSN 0008-4042
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Official URL: http://www.nrcresearchpress.com/doi/abs/10.1139/v9...
Related URL: http://dx.doi.org/10.1139/v91-116
Abstract
A general procedure for the synthesis of diverse cyclopentanols via free-radical cyclization of unsaturated 1,3-oxathiolanes and 1,3-oxathiolan-5-ones is described. The scope of these reactions, including preliminary rate studies that indicate that the 1,3-oxathiolan-5-ones cyclize at a useful rate (1.4×106 M−1 s−1 at 80°C), has been examined. This permits the rapid assembly, by intramolecular annulation, of various additional ring systems, including bicyclo[3.3.0]octanols, bicyclo[4.3.0]nonanols, and bicyclo[3.2.1]octanols for use in total synthesis.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to NRC Research Press. |
| Keywords: | Radical Cyclization; Oxathiolanes; Oxathiolanones |
| ID Code: | 58258 |
| Deposited On: | 31 Aug 2011 06:50 |
| Last Modified: | 31 Aug 2011 06:50 |
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