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DOI: 10.1055/s-2002-28509
Substitution Reactions of Hindered Cyclic Sulfamidates
Publication History
Publication Date:
14 May 2002 (online)
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Abstract
Five- and six-membered cyclic sulfamidates, [1,2,3]-oxathiazolidine- and [1,2,3]-oxathiazinane-2,2-dioxides, with the leaving group oxygen at sterically hindered centers were synthesized and treated with selected nucleophiles (azide, cyanide, fluoride, butylamine, sec-butylamine, tert-amylamine, and imidazole) in substitution reactions to demonstrate the general utility and limitations of these substrates. Substitutions adjacent to quaternary carbon centers were accomplished with relative ease. In contrast to the 4,4-dimethyl substituted 5-membered sulfamidate 1, which reacted with the entire set of nucleophiles, the more hindered 5-membered and 6-membered sulfamidates (7 and 6, respectively) reacted only with the first few of this set.
Key words
nucleophilic additions - steric hindrance - amines - substituent effects - cyclic sulfamidates
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