Title

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

RIS ID

95180

Publication Details

Gallego, G., Ariafard, A., Tran, K., Sandoval, D., Choi, L., Chen, Y., Yates, B. F., Tao, F. & Hyland, C. J. T. (2011). Titanium-mediated rearrangement of cyclopropenylmethyl acetates to (E)-halodienes. Organic and Biomolecular Chemistry, 9 (9), 3359-3363.

Abstract

TiCl4 and TiBr4 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 [TiX4OAc]− is under thermodynamic control, while the stereoselectivity is governed by kinetics.

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Link to publisher version (DOI)

http://dx.doi.org/10.1039/c0ob01046d