I've been following the e-mail discussions regarding your poster and have
some additional queries and comments. The different (and 'expected')
behaviour of the phenylglycinyl cyclohexene to the acetyl derivative is
especially strange. Are the conditions EXACTLY the same in both cases?
You have N-PSP/water for the acetyl case and N-PSP/CSA as the system for
the phenylglycinyl case, but that may just be a typographical change.
Having fallen foul of the 'readdition' of PhSeOH to olefins in attempted
selenoxide eliminations myself, I am wondering if the partial formation of
this species (from the hydrolysis of N-PSP) may explain the non-selectivity
of the acetyl case. Obviously, this can be ruled out if conditions are the
same in both cases. Although there are many papers on the addition of
PhSeOH (derived from many sources) to olefins, I know of none that would
allow one to estimate whether or not the selenenic acid may be susceptible
to directing effects. (This is based on my limited knowledge of the area,
such papers may well exist!). I'd be interested to hear your thoughts.