Ring Opening of Azetidinols by Phenols: Regiochemistry and Stereochemistry
Abstract
Ring opening of a series of 1-alkyl-4-bromophenol and 1-benzyl-3-azetidinols by 4-bromophenol without added base is reported. Opening of trans-2-methyl- and cis- and trans-2-phenyl-3-azetidinols is highly regioselective, if not regiospecific. The 2-methyl compounds open by cleavage of the N-C4 bond and the 2-phenyl compounds by cleavage of the N-C2 bond in a highly stereoselective, if not stereospecific, manner, which involves inversion of configuration at C2. The results are rationalized in terms of nucleophilic ring opening of the azetidinium ions. © 1994, American Chemical Society. All rights reserved.
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