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Topic: sulfonamide/tosyl confusion  (Read 2378 times)

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Offline kriggy

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sulfonamide/tosyl confusion
« on: September 23, 2013, 03:41:04 PM »
Hi guys, Im reading paper about Richman-Atkins macrocyclisation and it says:
"We have found that using that using performed bissulfonamide sodium salt...(2)" and picture shows:

And here comes the confusion, I thought that sulfonamide group is R-SOO-N-RR (sry for not using smiles, doesnt work for me) but the scheme shows Ts which is tosyl group AFAIK. So are those two same or not? Im realy confused..
Thanks a lot

Offline discodermolide

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Re: sulfonamide/tosyl confusion
« Reply #1 on: September 23, 2013, 03:49:47 PM »
tosyl is an abbreviation for para-tuoluene sulfonyl.
In the scheme you have a para-toluene sulphonamide sodium salt.
The other tosyl is also a para-toluene sulfonyl bit when attached to oxygen as in an alcohol it is an ester of sulfonic acid.
Sulfonamide
CC1=CC=C(S(=O)(N)=O)C=C1

Tosyl

CC1=CC=C(S(=O)(O)=O)C=C1
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Offline hinhthoi

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Re: sulfonamide/tosyl confusion
« Reply #2 on: September 24, 2013, 12:30:44 AM »
The compound 1, how does not contain -R group? Shouldn't it be -Ts?

Offline kriggy

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Re: sulfonamide/tosyl confusion
« Reply #3 on: September 24, 2013, 01:00:38 AM »
The compound 1, how does not contain -R group? Shouldn't it be -Ts?
Yes it is.

@disco: Yes exactly. So they just shortened the description in the text. Instead of bistoluensulphonamide salt they wrote bissulphonamide salt. That explains it. thanks

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