It should work, but weird things happened with asarone when trying to form the epoxide. I got a very odd viscous tar. The alkene group had completely reacted. I wonder if one should decrease the molar excess of Oxone (which is 2mol KHSO4 to 1mol alkene in the writeup, maybe something like 1.3mol KHSO4) when running it on asarone.
And uh, I post some info in Uemura's thread in Novel Discourse that would be best put here (sorry about that, I'm sure this is old info to bees who read -every- thread):
When the oxone reaction on asarone was attempted, the H2SO4 rearrangement seemed to chew the molecule apart, when NMR was run on the epoxide, it showed some interesting, but confusing info. It indicated that the methoxy groups were not cleaved by the oxone (good news, apparently oxone can do this in certain conditions), and the benzene group was not affected either. It also showed that the E-olefinic group was gone, and it looked as if there was some E/Z action going on (chiral centers in the epoxide), but the multiplicity did not work out correctly (the hydrogen containing one of the epoxide links, alpha to the methyl does not have the correct mulitiplicity). Something odd is going on. I'm going to tell my friend to run an anethole/oxone reaction (which I know works) to figure out if the same sort of spectra is generated. If not, then more tweaking of the oxone reaction will be needed for asarone.