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Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes


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

DOI: doi:10.1039/c0ob01046d


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:7
Deposited By:Chemistry
Deposited On:2011-08-30
Last Modified:2017-10-25

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