Issue 9, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Gary Gallego,a   Alireza Ariafard,*bc   Kiet Tran,a   David Sandoval,a   Leera Choi,a   Yi-Hsun Chen,a   Brian F. Yates,b   Fu-Ming Taoa  and  Christopher J. T. Hyland*ab  

* Corresponding authors

a Department of Chemistry and Biochemistry, California State University, Fullerton, CA, USA
E-mail: chyland@fullerton.edu
Tel: +1 (657) 278-2631

b School of Chemistry, University of Tasmania, School of Chemistry, University of Tasmania, Private Bag 75, Hobart TAS, Australia
E-mail: chris.hyland@utas.edu.au
Fax: +61 3 6226 2858
Tel: + 61 3 6226

c Department of Chemistry, Faculty of Science, Central Tehran Branch, Islamic Azad University, Shahrak Gharb, Tehran, Iran

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.

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

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Article information

DOI
https://doi.org/10.1039/C0OB01046D
Article type
Paper
Submitted
18 Nov 2010
Accepted
03 Feb 2011
First published
07 Feb 2011

Org. Biomol. Chem., 2011,9, 3359-3363

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

G. Gallego, A. Ariafard, K. Tran, D. Sandoval, L. Choi, Y. Chen, B. F. Yates, F. Tao and C. J. T. Hyland, Org. Biomol. Chem., 2011, 9, 3359 DOI: 10.1039/C0OB01046D

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