Several organic mechanisms I know involve [2+2] cycloadditions and retro-[2+2] cycloadditions, namely:

  • The Wittig reaction
  • Hydroboration of an alkene
  • Olefin metathesis (using Grubbs' catalyst)

How are these in accordance with the Woodward–Hoffmann rules? I think that there are two $(4q+2)_s$ components and that's not an odd number, which is the criterion for a reaction to be thermally allowed.

  • $\begingroup$ en.wikipedia.org/wiki/Olefin_metathesis#Reaction_mechanism $\endgroup$ – Mithoron May 24 '15 at 12:57
  • $\begingroup$ So it happens, regardless of the forbidden symmetry. $\endgroup$ – EJC May 24 '15 at 16:28
  • 4
    $\begingroup$ The Woodward-Hoffmann rules for pericylic reactions assumes essentially that you can describe the orbitals in terms of Huckel approximations, which is definitely not the case for a Ru catalyst. $\endgroup$ – J. LS May 24 '15 at 21:06
  • $\begingroup$ Could you elaborate as an answer? $\endgroup$ – EJC May 25 '15 at 7:36
  • 1
    $\begingroup$ I think you can try - don't be afraid :) $\endgroup$ – Mithoron Aug 9 '15 at 16:28

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.