Jump to main content
Jump to site search

Issue 9, 2011
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Nov 2010, accepted on 03 Feb 2011 and first published on 07 Feb 2011


Article type: Paper
DOI: 10.1039/C0OB01046D
Citation: Org. Biomol. Chem., 2011,9, 3359-3363
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements