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Ring Expansion of 2‐(1‐Hydroxyalkyl)azetidines to 4‐(2‐Chloroethyl)oxazolidinones
Author(s) -
Couty François,
Drouillat Bruno,
Lemée Frédéric
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001375
Subject(s) - chemistry , azetidine , ring (chemistry) , alcohol , substitution (logic) , scope (computer science) , carbonate , medicinal chemistry , stereochemistry , organic chemistry , computer science , programming language
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.