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

Journal Article


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.

UOW Authors


  •   Gallego, Gary (external author)
  •   Ariafard, Alireza (external author)
  •   Tran, Kiet (external author)
  •   Sandoval, David (external author)
  •   Choi, Leera (external author)
  •   Chen, Yi-Hsun (external author)
  •   Yates, Brian F. (external author)
  •   Tao, Fu-Ming (external author)
  •   Hyland, Christopher

Publication Date


  • 2011

Citation


  • 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.

Scopus Eid


  • 2-s2.0-79954428337

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2322

Number Of Pages


  • 4

Start Page


  • 3359

End Page


  • 3363

Volume


  • 9

Issue


  • 9

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.

UOW Authors


  •   Gallego, Gary (external author)
  •   Ariafard, Alireza (external author)
  •   Tran, Kiet (external author)
  •   Sandoval, David (external author)
  •   Choi, Leera (external author)
  •   Chen, Yi-Hsun (external author)
  •   Yates, Brian F. (external author)
  •   Tao, Fu-Ming (external author)
  •   Hyland, Christopher

Publication Date


  • 2011

Citation


  • 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.

Scopus Eid


  • 2-s2.0-79954428337

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2322

Number Of Pages


  • 4

Start Page


  • 3359

End Page


  • 3363

Volume


  • 9

Issue


  • 9