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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
Author(s) -
Plagge Herbert,
Manicone Nico,
Otto HansHartwig
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490144
Subject(s) - chemistry , electrophile , tosyl , triazine , surface modification , ring (chemistry) , isocyanate , halogen , electrophilic substitution , substitution reaction , organic chemistry , medicinal chemistry , alkyl , catalysis , polyurethane
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.