32102-08-2Relevant academic research and scientific papers
Mixed carboxylic-sulfonic anhydride in reaction with imines: A straightforward route to water-soluble β-lactams via a Staudinger-type reaction
Bakulina, Olga,Dar'In, Dmitry,Krasavin, Mikhail
, p. 3989 - 3998 (2018/06/08)
The first example of employing a mixed carboxylic-sulfonic anhydride in reaction with imines is reported. Unlike its well-studied isostere homophthalic anhydride, benzo[c][1,2]oxathiin-3(4H)-one 1,1-dioxide gave no product of a formal [4 + 2] cycloaddition and only followed an alternative reaction pathway toward β-lactams, presumably, via a formal [2 + 2] cycloaddition (a Staudinger-type reaction). Optimized reaction conditions involve the use of triethylamine as a base promoter, which also allows isolating the product β-lactam benzene sulfonic acids as respective triethylammonium salts by conventional column chromatography. The reaction shows some preference to trans-isomer formation; pure diastereomers can be isolated in some cases.
INTRAMOLECULAR SULFONAMIDE-CARBOXAMIDE REARRANGEMENT.
Hovius, Klaas,Wagenaar, Anno,Engberts, Jan B. F. N.
, p. 3137 - 3140 (2007/10/02)
Several o-carboxy-N,N-dialkylbenzenesulfonamides rearrange intramolecularly to o-chlorosulfonyl-N,N-dialkylbenzamides upon treatment with an excess of thionyl chloride in an apolar solvent.
