Ring Expansion of 2-(1-Hydroxyalkyl)azetidines to 4-(2-Chloroethyl)oxazolidinones

✍ Scribed by François Couty; Bruno Drouillat; Frédéric Lemée

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 557 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201001375

✦ Synopsis

Abstract

2‐(1‐Hydroxyalkyl)azetidines react with bis(trichloromethyl) carbonate (BTC) after basic treatment to afford 4‐(2‐chloroethyl)oxazolidinones. The scope of this rearrangement was examined in detail and its efficiency was shown to depend on the class of the reacting alcohol and on the substitution pattern on the azetidine ring.