One-carbon ring expansion of azetidines via ammonium ylide [1,2]-shifts: a simple route to substituted pyrrolidines

Author
Bott, Tina
Vanecko, John A.
West, F. G.
Faculty Advisor
Date
2009
Keywords
pyrrolidines , electromagnetic radiation , nitrogen , cations , allyl group
Abstract (summary)
Simple N-substituted azetidines were heated with diazocarbonyl compounds in the presence of catalytic Cu(acac)2 to furnish substituted pyrrolidines via Stevens [1,2]-shift. In all but two examples, complete selectivity was seen for ring expansion rather than migration of the other exocyclic group on the azetidinium nitrogen. The two exceptions, observed with ylides substituted with two carbonyl groups and lacking a stabilizing group at the 2-position of the azetidine, underwent exocyclic benzyl migration in preference to ring expansion.
Publication Information
Bott, T. M. Vanecko, J. A. West F. G. (2009). One-carbon ring expansion of azetidines via ammonium ylide [1,2]-shifts: A simple route to substituted pyrrolidines. Journal of Organic Chemistry, 74(7), 2832-2836. https://doi.org/10.1021/jo9001323
DOI
Notes
Item Type
Article
Language
English
Rights
All Rights Reserved