82358-07-4Relevant articles and documents
Sterically constrained 'roofed' 2-thiazolidinones as excellent chiral auxiliaries
Hoshimoto,Matsunaga,Kunieda
, p. 1541 - 1544 (2000)
The 'roofed' chiral 2-thiazolidinones, which are sterically congested and conformational rigid, and which are prepared by the [4 + 2] cycloaddition of 2-thiazolone to the cyclic dienes, dimethylanthracene and hexamethylcyclopentadiene, followed by optical
Hydroxylamine as an oxygen nucleophile: Substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides
Kamps, Jos J. A. G.,Belle, Roman,Mecinovi?, Jasmin
, p. 1103 - 1108 (2013/03/28)
Benzothiazole-2-sulfonamides react with an excess of hydroxylamine in aqueous solutions to form 2-hydroxybenzothiazole, sulfur dioxide, and the corresponding amine. Mechanistic studies that employ a combination of structure-reactivity relationships, oxygen labeling experiments, and (in)direct detection of intermediates and products reveal that the reaction proceeds via oxygen attack, and that oxygen incorporated in the 2-hydroxybenzothiazole product derives from hydroxylamine. The reaction, which is performed under mild conditions, can be used as a deprotection method for cleavage of benzothiazole-2-sulfonyl-protected amino acids.