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Author: Subject: Sulfonic Acid Groups to "Thioamines"
Amoled
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[*] posted on 2-10-2018 at 12:37
Sulfonic Acid Groups to "Thioamines"


Hey, would it be possible, to turn sulfonic acid groups, like in Taurine

Screenshot_20181002-223350.jpg - 186kB

into "Thioamines" or how you would call it - like this

Screenshot_20181002-223500.jpg - 107kB

via Leuckart-Wallach for example?

And if not, is there any specific reason?
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[*] posted on 2-10-2018 at 12:59


Why is S 4-valent in your molecule?



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clearly_not_atara
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[*] posted on 2-10-2018 at 13:00


Compounds with two geminal YHx substituents where Y = (N, O, Cl, F, S, Br, I) x = (0,1,2) tend to be very unstable, eliminating YH(x+1). So your example compound would eliminate ammonia. However, the general class of compounds does exist:

https://www.ncbi.nlm.nih.gov/m/pubmed/14871110/

Edit: better link

[Edited on 2-10-2018 by clearly_not_atara]




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[*] posted on 2-10-2018 at 13:08


Sulfonamide of taurine is probably known. what you have drawn is some vastly more obscure compound which would be best described by replacing the HO-S with a S=O. These are apparently called sulfonimidamides and are not prepared by reductive amination of some S=O compound and neither are sulfonamides.
https://onlinelibrary.wiley.com/doi/10.1002/adsc.201800273

https://www.organic-chemistry.org/Highlights/2004/24December...
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