Chemistry of oxaziridines. 13. Synthesis, reactions, and properties of 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides

Autor:	Mark E. Harakal, John P. McCauley, Dhiru B. Vashi, James C. Towson, Donald J. Gosciniak, Franklin A. Davis, R. ThimmaReddy
Rok vydání:	1990
Předmět:	Steric effects chemistry.chemical_compound chemistry Reagent Yield (chemistry) Organic Chemistry Oxidizing agent Organic chemistry Sulfoxide Reactivity (chemistry) Selectivity Sulfone
Zdroj:	The Journal of Organic Chemistry. 55:1254-1261
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00291a028
Popis:	The synthesis, properties, and reactions of 3-substituted 1,2-benzisothiazole 1,1-dioxide oxides 8, highly stable examples of 3,3-disubstituted N-sulfonyloxaziridines 3, are described. These new N-sulfonyloxaziridines are prepared in high yield by oxidation of the corresponding sulfonimines 7. Kinetic studies of the oxidation of sulfoxides to sulfones and the epoxidation of limonene reveal that these new oxidizing reagents exhibit reduced reactivity, but greater selectivity, compared to oxaziridines, in their oxygen-transfer reactions due to greater steric hindrance of the active-site oxygen. (8-dioxide-10,10-oxireno [2,3-b] benzisothiazoles)
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::57dbd0c1e81734e59adf2cd4cb994873 https://doi.org/10.1021/jo00291a028 Zobrazit plný text záznamu