An efficient flow-photochemical synthesis of 5H-furanones leads to an understanding of torquoselectivity in cyclobutenone rearrangements
Harrowven, David C., Mohamed, Mubina, Gonçalves, Théo P., Whitby, Richard J., Bolien, David and Sneddon, Helen F. (2012) An efficient flow-photochemical synthesis of 5H-furanones leads to an understanding of torquoselectivity in cyclobutenone rearrangements. Angewandte Chemie International Edition, 51, (18), 4405-4408. (doi:10.1002/anie.201200281).
Download
Full text not available from this repository.
Description/Abstract
4-Hydroxycyclobutenones were efficiently transformed into 5H-furanones using an inexpensive flow-photochemical setup. The results challenge the notion that this and the related thermochemical rearrangement display torquoselectivity in their electrocyclic opening to a vinylketene intermediate. Selectivity in the photochemical rearrangement is due a dichotomous reactivity of the (E)- and (Z)-vinylketene intermediates.
| Item Type: | Article |
|---|---|
| ISSNs: | 1433-7851 (print) 1521-3773 (electronic) |
| Keywords: | cyclobutenones, density functional calculations, photochemistry, rearrangements, small ring systems |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Natural and Environmental Sciences > Chemistry |
| Item ID: | 337265 |
| Date Deposited: | 20 Apr 2012 12:11 |
| Last Modified: | 26 Apr 2013 05:43 |
| Contributors: | Harrowven, David C. (Author) Mohamed, Mubina (Author) Gonçalves, Théo P. (Author) Whitby, Richard J. (Author) Bolien, David (Author) Sneddon, Helen F. (Author) |
| Funder: | GlaxoSmithKline, ERDF (IS:CE-Chem InterReg IVa), EPSRC |
| Date: | 27 April 2012 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/337265 |
Actions (login required)
 |
View Item |
