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Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: Synthesis of N-Substituted 4,4-dimethyl-1,2-thiazetidin-3-one 1,1-dioxides, and a new base-catalyzed rearrangement to thiazolidin-4-one 1,1-dioxides

✍ Scribed by Dietmar Glasl; Hans-Hartwig Otto; Grety Rihs

Publisher
John Wiley and Sons
Year
1997
Tongue
German
Weight
888 KB
Volume
80
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Alkylation of 3‐oxo‐1,2‐thiazetidine 1,1‐dioxide 2 yields the N‐alkylated 3‐oxo‐β‐sultams 3a‐i. Solvolysis with NaOH or NH~3~ selectively opens the NS bond forming the sulfonate carboxamides 4 and the sulfonamidocarboxamides 7, respectively. Furthermore, the hitherto unknown compounds of type 5 are prepared, representing a strained four‐membered ring with a diacylated, sulfonated N‐atom. Depending upon the reaction conditions, 3b‐d and 3g are rearranged by base‐catalyzed reactions into the substituted 4‐oxothiazolidine 1,1‐dioxides 9 or 10. Structures are elucidated by spectroscopic methods, established by crystal‐structure analyses, and a possible way of formation is proposed. Furthermore, some side reactions and transformations are reported.

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Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: 3-Acetoxy-1,2-thiazetidine 1,1-Dioxide, Synthesis and Reactions with C-Nucleophiles
✍ Schwenkkraus, Peter ;Merkle, Stefan ;Otto, Hans-Hartwig 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 670 KB

## Abstract __N__‐Silylated 3‐acetoxy‐1,2‐thiazetidine 1,1‐dioxide (5) is prepared from L‐cystine. Reactions of 5 with silyl enol ethers yield C‐3‐substituted β‐sultams 6, 12 and 15. Desilylation of 6 affords 7, which undergoes photochemical cyclization to give the bicyclic β‐sultam 10. In the cour

Properties and Reactions of Substituted
Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: 4-Alkylidene-β-sultams
✍ Müller, Martin ;Otto, Hans-Hartwig 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 615 KB

## Abstract 4‐α‐Hydroxyalkylated β‐sultams 1/5 are transformed into 4‐alkylidene‐β‐sultams 4/7 by elimination and desilylation reactions. Another route to an exocyclic double bond in the β‐sultam system has been found to be the Peterson olefination starting from 4 silylated β‐sultams 8, 10, and 11.