R. H. Higgins, W. J. Faircloth, R. G. Baughman
Apr 1, 1994
Citations
0
Influential Citations
20
Citations
Journal
Journal of Organic Chemistry
Abstract
Ring opening of a series of 1-alkyl- 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 inver- sion of configuration at C2. The results are rationalized in terms of nucleophilic ring opening of the azetidinium ions