Ok, I've read a bit more on halohydrins. My organic chemistry book states that usually halohydrins are formed using NXS--but that X2 will also work (even tho it's more dangerous and difficult to handle). It explicitly states that halohydrin formation doesn't take place by direct reaction of an alkene with HOCl (I wish I had read my organic chem book before experimenting), rather the addition is done indirectly by the reaction of the alkene with Cl2 in the presence of water (I think this explains why the smell of bleach was gone once the alkene was added, and why I never saw a big temperature jump--because the rate of reaction was so unbearably slow). This boils down to the realization that some sort of catalyst must be used for even non-enatioselective epoxide formation, as the intermediate chlorohydrin will not form (although, if it did, it would apparently rearrange in the basic conditions).
So that's somewhat good news, and somewhat bad news. It makes the epoxide formation a bit more tricky, but not necessarily impossible. HCl onto bleach would generate in situ chlorine gas, and making that solution basic with NaOH would rearrange to the epoxide. It's still might be able to be turned into a one pot synth, can't get much better than that.
But... this is the part I don't like. It says that in practice most alkenes are insoluble in water and the reaction is often carried out in aqueous DMSO. Does this mean that the reaction has to be carried out in aqueous DMSO (or as in PS post with electrolytic generation of chlorine, a tertiary alkanol)?
-- note --
It seems that it does not have to be carried out in aqueous DMSO/t-butyl alcohol, I ran across a patent (seaching for epoxide/alkene/hypochlorous) that does not use any organic solvent. But I do have a few questions, in all the patents talking about forming halohydrins from alkenes, it seems that they stress low-chloride concentrations to avoid chlorination of alkyl groups. Will this be a significant problem with my suggested method? Would it then make more sense to generate the chlorine externally? (or maybe switch the approach entirely, say to using bromine in aqueous DCM?)
Btw, does anyone know if I can use DCM when generating chlorine gas in the above way? Is the kinetics of chlorine reacting with DCM slow enough that it won't be chlorinated?