November 28, 2022, 11:24:59 PM
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Topic: Use of sulfonyl fluorides to produce sulfonyl Phosphonates  (Read 2837 times)

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Offline rolnor

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Re: Use of sulfonyl fluorides to produce sulfonyl Phosphonates
« Reply #15 on: July 13, 2022, 05:40:31 PM »
Yes, the double bond would be nice if possible, cleave to aldehyde, then wittig. Or metathesis reaction. The acidic proton in the sulphone-phosphonate makes som limitation, you easily get polymer if you have an electrophile present in the other end of the molecule and use basic conditions. Or ringclosure.
You could make the first step with sodium sulfide, to get the phosphonate-sulfide, then you can put on different alkyl groups, sulfur being a powerfull nucleophile, then oxidize with oxone. But it will be a smelly business. You can also use LDA+the methyl phosphonate , then add elemental sulfur, then one-pot add the alkyl halide to the formed lithium sulfide to form the sulfide of your choice. Then oxidize  with oxone, three one-pot steps.

Offline Babcock_Hall

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Re: Use of sulfonyl fluorides to produce sulfonyl Phosphonates
« Reply #16 on: July 19, 2022, 06:43:17 PM »
I tried the reaction of diethyl methylphosphonate, LiHMDS, and PhSO2F twice.  The first time did not go well, and there were several things that might have contributed.  Yet the second time gave me a crude yield of 72% and what looks like almost a pure compound by P-31 and H-1 NMR. 

Offline rolnor

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Re: Use of sulfonyl fluorides to produce sulfonyl Phosphonates
« Reply #17 on: July 20, 2022, 06:27:58 AM »
Fantastic! Nice! You really need some success after so much hard work.

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