Hans Hettler

3-Oxo-2,3-dihydrobenz[d]isothiazole-1,1-dioxide (Saccharin) and Derivatives

Publisher Summary This chapter focuses on the 3-Oxo-2,3-dihydrobenz[d]isothiazole-1, l-dioxide (saccharin) and in particular with such derivatives that are formally on the same level of oxidation, example, 3-thioxo- 2,3-dihydrobenz [d]isothiazole-1 1-dioxide (thiosaccharin) and the so-called “pseudosaccharins. The objective is to report on the more recent developments in this area, focusing on preparative aspects. The nomenclature and structures and physical properties of saccharin are discussed. Saccharin became an industrial product as the first noncarbohydrate sweetener, and it is still holding an important position in the market. Substantial quantities are used as additives in the electroplating industry. Saccharin and its sodium salt have found extensive use as nonnutritive sweetening agents. Preparation and properties of saccharin system, 3-alkoxy and 3-aryloxybenz[ d ]isothiazole- 1,1-dioxides, 3-aminobenz[d]isothiazole- 1,l-dioxide are discussed. Thiosaccharin system is also discussed. 3-alkoxy- and 3-aryloxybenz[d]isothiazole-l, 1-dioxides, “pseudosaccharin ethers,” are obtained by reacting 3-chlorobenz- [dlisothiazole-1, l-dioxide with the corresponding aliphatic or aromatic alcohols. Such derivatives are usually crystalline, and have been recommended for the characterization of alcohols and phenols, and for protecting alcoholic functions.

Charakterisierung von primÄren und sekundÄren Aminen mit Pseudosaccharinchlorid

SummaryPseudosaccharin chloride reacts with primary and secondary amines to yield crystalline compounds of the amidine type, which are exceptionally stable.Since the rate of reaction with amines is faster than hydrolysis the reaction can be carried out in the presence of water as well. Pseudosaccharin ethers are cleaved by primary and secondary amines to give the same compounds.ZusammenfassungPseudosaccharinchlorid reagiert mit primÄren und sekundÄren Aminen zu gut kristallisierenden Verbindungen des Amidintypes, die sehr stabil sind. Die Reaktion kann auch in Gegenwart von Wasser ausgeführt werden, da ihre Geschwindigkeit höher ist als die der Hydrolyse. PseudosaccharinÄther werden von primÄren und sekundÄren Aminen unter Bildung derselben Verbindungen gespalten.

Formation of cyclodextrin inclusion compounds of stable nitroxide radicals as monitored by electron-spin resonance spectra

Abstract Hyperfine coupling constants and rotational correlation times, calculated from electron-spin resonance spectra of cyclodextrins incubated with stable nitroxide radicals, indicate inclusion compound formation of β- and γ-cyclodextrin with certain nitroxide radicals. In contrast, α-cycledextrin exhibits no effect on the spectra of the radicals, probably because its central cavity is too small to form such inclusion compounds. Furthermore, one 1:1 molar ratio complex of β-cyclodextrin and a nitroxide radical (isolated as crystalline precipitate and identified both by combustion analysis and ir measurements) is shown by electron-spin resonance data to be an inclusion compound.