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An explanation for the failure of aminomethanesulfonic acid to form sulfonamides. Acyl chloride-promoted generation of α-carboxamidoalkylating electrophiles.

✍ Scribed by Gregory R. Moe; Lawrence M. Sayre; Philip S. Portoghese


Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
235 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis


Attempted N,N-dibenzoylation of aminomethanesulfonic acid results in C-S bond cleavage, generating synthetically useful a-bensamidomethylatinq electrophiles. The importance of this observation in regard to the reported failures to prepare sulfonamide analogs of peptides is discussed.