September 29, 2023, 04:30:15 PM
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Topic: Bis or poly tertiary thiols  (Read 926 times)

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Offline wildfyr

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Bis or poly tertiary thiols
« on: March 28, 2019, 11:56:11 AM »
Whats the best way you can think of to create bis, tris, or poly tertiary thiols?

I have a good pathway to get there from isobutyryl, but what I'd really like is to have just a multi-tertiary alkyl molecule. Being alpha to the carbonyl may negatively affect the reactivity I want.

The most useful reaction for generating thiols I've found is using potassium thioacetate with a bromide or other good LG (like a tosylate, derived from the alcohol). You get the thioester, which is base hydrolyzed with KOH to get a thiol.

My idea so far is to use a methyl Grignard on a diketone to get a bis tertiary alcohol, which is then either brominated or tosylated, and then turned into a thiol with thioacetate. But... I'd rather not do a Grignard.

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