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Synthesis 2002(7): 0859-0864
DOI: 10.1055/s-2002-28509
PAPER
© Georg Thieme Verlag Stuttgart · New York

Substitution Reactions of Hindered Cyclic Sulfamidates

Jeffrey J. Posakonya, Timothy J. Tewson*b
a University of Washington, Department of Radiology Imaging Research Laboratory, Rm NW041, Box 356004, 1959 NE Pacific St., Seattle, WA 98195, USA
b University of Iowa PET, Imaging Center, Department of Radiology, 0911Z JPP, 200 Hawkins Drive, Iowa City, Iowa, 52242-1007, USA
Fax: +1(319)3536512; e-Mail: timothy-tewson@uiowa.edu;
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Publication History

Received 18 March 2001
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