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Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: Functionalization and Reactions at C(4) of the β-Sultam

✍ Scribed by Herbert Plagge; Nico Manicone; Hans-Hartwig Otto

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
248 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The introduction of functional groups at the 4‐position of the β‐sultam ring was realized by the synthesis of mono‐ and disubstituted derivatives by reactions of N‐silylated β‐sultams with electrophiles in the presence of BuLi or LDA. As electrophiles, ketones, chlorosilanes, a β‐sultam, CO~2~, chloroformiate, halogen, azodicarboxylate, phenyltriazoledione, tosyl azide, 1,3,5‐triazine, propyl nitrate, and phenyl isocyanate were used. Furthermore, a number of derivatives of these substitution products were synthesized. All products were characterized by standard spectroscopic methods, and conformations were studied, supported by calculation.

📜 SIMILAR VOLUMES

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.

Properties and reactions of substituted
Properties and reactions of substituted 1,2-thiazetidine 1,1-dioxides: Acylation of β-sultams at C-4, reduction of 4-acyl-β-sultams, and stereochemistry of 4-(α-hydroxyalkyl)-β-sultams
✍ Müller, Martin ;Otto, Hans-Hartwig 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 English ⚖ 827 KB

## Abstract Acylation of __N__‐silylated and 2,3‐substituted 1,2‐thiazetidine 1,1‐dioxides (β‐sultams) results in the formation of 4‐acylated β‐sultams 2 and 8. The desilylation of 2 to 3 is easily done with TBAF either on silica gel or in ethanolic solution. The acylated β‐sultams are reduced by s