𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: 4-Alkylidene-β-sultams

✍ Scribed by Müller, Martin ;Otto, Hans-Hartwig

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
615 KB
Volume
1992
Category
Article
ISSN
0947-3440

No coin nor oath required. For personal study only.

✦ Synopsis

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. The elimination‐reaction sequence yields stereochemically defined products with either E or Z configuration but by use of the Peterson reaction we have always obtained mixtures of diastereomers, which have to be separated. The stereochemistry of all products is elucidated by spectroscopic methods.

📜 SIMILAR VOLUMES

Properties and Reactions of Substituted
Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: Functionalization and Reactions at C(4) of the β-Sultam
✍ Herbert Plagge; Nico Manicone; Hans-Hartwig Otto 📂 Article 📅 2004 🏛 John Wiley and Sons 🌐 German ⚖ 248 KB

## 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

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