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Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes
Citation
Gallego, G and Ariafard, A and Tran, K and Sandoval, D and Choi, L and Chen, YH and Yates, BF and Tao, FM and Hyland, CJT, Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes, Organic & Biomolecular Chemistry, 9, (9) pp. 3359-3363. ISSN 1477-0520 (2011) [Refereed Article]
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Copyright Statement
Copyright 2011 Royal Society of Chemistry
Abstract
TiCl(4) and TiBr(4) rapidly transform cyclopropenylmethyl acetates to (E)-halodienes via ring-opening to allyl-vinyl cations. DFT calculations suggest that the regioselectivity of the halogenation of this cationic intermediate by [TiX(4)OAc](-) is under thermodynamic control, while the stereoselectivity is governed by kinetics.
Item Details
| Item Type: | Refereed Article |
|---|---|
| Research Division: | Chemical Sciences |
| Research Group: | Organic Chemistry |
| Research Field: | Organic Chemical Synthesis |
| Objective Division: | Expanding Knowledge |
| Objective Group: | Expanding Knowledge |
| Objective Field: | Expanding Knowledge in the Chemical Sciences |
| UTAS Author: | Ariafard, A (Associate Professor Alireza Ariafard) |
| UTAS Author: | Yates, BF (Professor Brian Yates) |
| UTAS Author: | Hyland, CJT (Dr Chris Hyland) |
| ID Code: | 72639 |
| Year Published: | 2011 |
| Web of Science® Times Cited: | 5 |
| Deposited By: | Chemistry |
| Deposited On: | 2011-08-30 |
| Last Modified: | 2017-10-25 |
| Downloads: | 0 |
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