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

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dc.contributor.authorBott, Tina
dc.contributor.authorVanecko, John A.
dc.contributor.authorWest, F. G.
dc.date.accessioned2021-05-14
dc.date.accessioned2022-05-31T01:43:36Z
dc.date.available2022-05-31T01:43:36Z
dc.date.issued2009
dc.description.abstractSimple 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.
dc.description.urihttps://library.macewan.ca/full-record/edo/37581357
dc.identifier.citationBott, 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
dc.identifier.doihttps://doi.org/10.1021/jo9001323
dc.identifier.urihttps://hdl.handle.net/20.500.14078/2273
dc.languageEnglish
dc.language.isoen
dc.rightsAll Rights Reserved
dc.subjectpyrrolidines
dc.subjectelectromagnetic radiation
dc.subjectnitrogen
dc.subjectcations
dc.subjectallyl group
dc.titleOne-carbon ring expansion of azetidines via ammonium ylide [1,2]-shifts: a simple route to substituted pyrrolidines
dc.typeArticle
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