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Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes
journal contribution
posted on 2023-05-17, 07:52 authored by Gallego, G, Alireza AriafardAlireza Ariafard, Tran, K, Sandoval, D, Choi, L, Chen, YH, Brian YatesBrian Yates, Tao, FM, Hyland, CJTTiCl(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.
History
Publication title
Organic & Biomolecular ChemistryVolume
9Issue
9Pagination
3359-3363ISSN
1477-0520Department/School
School of Natural SciencesPublisher
Royal Society of ChemistryPlace of publication
Thomas Graham House, Science Park, Milton Rd, Cambridge, England, Cambs, Cb4 0WfRights statement
Copyright 2011 Royal Society of ChemistryRepository Status
- Restricted