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Reactions of 1,2-thiazetidine 1,1-dioxides with organometallics: β-Elimination and NS bond cleavage

✍ Scribed by Tetsuo Iwama; Tadashi Kataoka; Osamu Muraoka; Genzoh Tanabe

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 964 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00239-7

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✦ Synopsis

Reactions of 4-nonsubstituted l~-sultams 1 with methyilithium gave only (E)vinylsulfonamides 2, whereas 2-aminoethyl sulfones 3 were obtained as minor products by use of methylmagnesium bromide. Reactions of 4-monosubstituted [3-sultams 6 with organolithiums gave (E)-vinylsulfonamides 7 stereoseleetively regardless of the configuration of 3-and 4-substituents. Treatment of 4,4-dimethyl-13-sultam 8a with methylmagnesium bromide and methyllithium provided 2aminoethyl sulfone 9 and bis-sulfone 10, respectively, and isopropyl phenyl sulfone 11 was obtained by use of phenyllithium or phenylmagnesium bromide.

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