Skip NavigationSkip to Content
Return Return to Search Results

Regioselective epoxide ring-opening using boron trifluoride diethyl etherate: DFT study of an alternative mechanism to explain the formation of syn-fluorohydrins

  1. Author:
    Mendez, P. S.
    Cachau, R. E.
    Seoane, G.
    Ventura, O. N.

  2. Author Address

    Mendez, Patricia Saenz, Seoane, Gustavo] UdelaR, Fac Chem, Dept Organ Chem, Phys Organ Chem & Bioproc Grp, Montevideo 11800, Uruguay. [Mendez, Patricia Saenz, Cachau, Raul E.; Ventura, Oscar N.] UdelaR, Fac Chem, DETEMA, Computat Chem & Biol Group, Montevideo 11800, Uruguay. [Cachau, Raul E.] SAIC Frederick Inc, Natl Canc Inst Frederick, Adv Biomed Comp Ctr, Frederick, MD 21702 USA.
    1. Year: 2009
  2. Journal: Journal of Molecular Structure-theochem
    1. 904
    2. 1-3
    3. Pages: 21-27
  4. Type of Article: Article
  1. Abstract:

    Ring-opening of epoxides with boron trifluoride yielding syn-fluorohydrins was investigated using density functional methods (PBE) and two different basis sets (6-31G(d) and 6-311++G(2df,2pd), both in gas phase and simulating the bulk solvent using the PCM method. The only mechanism previously suggested for the formation of fluorohydrins from epoxides is an S-N 1-like one. We propose in this work a new mechanism, in which bond breaking in the epoxide is Coupled to fluorine transfer, yielding the fluorohydrine with retention of configuration through a single transition state. (c) 2009 Elsevier B.V. All rights reserved.

    See More

  1. Keywords:

External Sources

  1. View Full Text
  2. DOI: 10.1016/j.theochem.2009.02.023
  3. No sources found.

Library Notes

  1. No notes added.
NCI at Frederick

You are leaving a government website.

This external link provides additional information that is consistent with the intended purpose of this site. The government cannot attest to the accuracy of a non-federal site.

Linking to a non-federal site does not constitute an endorsement by this institution or any of its employees of the sponsors or the information and products presented on the site. You will be subject to the destination site's privacy policy when you follow the link.

ContinueCancel