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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, CJT
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.

History

Publication title

Organic & Biomolecular Chemistry

Volume

9

Issue

9

Pagination

3359-3363

ISSN

1477-0520

Department/School

School of Natural Sciences

Publisher

Royal Society of Chemistry

Place of publication

Thomas Graham House, Science Park, Milton Rd, Cambridge, England, Cambs, Cb4 0Wf

Rights statement

Copyright 2011 Royal Society of Chemistry

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  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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    In Copyright

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