Health & Environmental Research Online (HERO)


Print Feedback Export to File
7603545 
Journal Article 
Oxidative Cyclization of Sulfamate Esters Using NaOCl - A Metal-Mediated Hoffman-Löffler Freytag Reaction 
Zalatan, DN; Du Bois, J; , 
2009 
1 
Synlett
ISSN: 0936-5214
EISSN: 1437-2096 
GEORG THIEME VERLAG KG 
STUTTGART 
2009 
1 
143-146 
English 
19319207 
WOS:000262526300033 
Intramolecular C-H amination with sulfamate esters occurs under the action of dinuclear Rh catalysts and iodine(III) oxidants, and has recently emerged as a powerful tool for synthesis. Insights gained through mechanistic studies of this process suggest that other terminal oxidants, including common halogenating agents such as NaOCl, could function to promote the cyclization reaction. Results described in this report demonstrate that the combination of NaOCl and 3 mol% Rh(2)(oct)(4) is effective in select cases for converting sulfamate substrates to the corresponding [1,2,3]-oxathiazinane-2,2-dioxide heterocycles. The mechanism for C-H functionalization, however, is distinct from that induced by hypervalent iodine reagents and likely involves the intermediacy of an N-centered radical.