[incorporealist]

So I'm not an O-Chem guy intrinsically, but I have a project I want to work on that's going to require me to thiolate an allyl group. I don't really care about selectivity, stereo-,regio- or otherwise, or if the double bond remains intact or not. I just need a thiol group somewhere on it, without destroying the aromatic ring it's attached to. I've looked through the resources I have available but it's either too easy or too difficult to come up in any of my searches.

Any ideas?

[wildfyr]

Where on the allyl group? Can you give us at least a basic framework to start with? How is it attached to aromatic ring? Is it a free thiol, or a thio ether you want to end up with?

[incorporealist]

I'm looking for a free thiol, and it is simply an allyl group attached to a phenyl ring. Here's a graphic to give you an idea of what I'm looking for, though if for some reason it would be easier to leave the double bond intact, that would be perfectly acceptable.

[wildfyr]

Do hydrohalogenation (such as with HBr) to give a benzylic bromide, then use potassium thioacetate to attack the benzyl halide, followed by KOH to cleave the acetate, giving the aryl potassium thiolate, then acidify to yield a secondary thiol.

It will also probably stink horribly.

You only need to isolate after benzylic bromide step and after the final acid step.

[incorporealist]

That's fantastic, thank you so much!!!

Sulfur chemistry always stinks, I have a pretty decent hood at least.