I am very interested by your hydroxyselenation poster, and particularly by
your challenge to explain the results. I think it is possible to explain
the results without needing to assume two rather different reactions go at
the same speed.
Your first mechanism suggests that an intermediate is formed, which may
lead to two products:
[figure1]
It may be that the reaction goes just by a mechanism of the second type.
When the acetate is axial, it withdraws electrons from the double bond, and
so deactivates it. If the acetate is equatorial, it is orthogonal to the
double bond, and so no longer deactivates it. However, it need have no
other effect.
[figure2]
It is unlikely that two different reactions will go at the same rate under
all conditions of temperature and solvent. The mechanism I suggest can be
shown to be wrong, by repeating the experiment with different solvents and
temperatures. My mechanism suggests that the ratio should always be 1:1.
The mechanism in the poster would probably suggest that the ratio should
vary with solvent and temperature. The idea could also be tested by doing
the reaction on fluorocyclohexene. The fluoride should have a similar
electronic effect to the acetate, deactivating the axial conformation, but
would not be able to deliver the selenium, as in the mechanism of the
poster. It should, therefore, also give a 1:1 mixture.
I have attached to schemes to this message as tgf files. This message can
also be read in full on http://www.ch.cam.ac.uk/MMRG/ECTOC/sweeney.html
Yours sincerely,
Jonathan Goodman
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