Carbene reactions of alpha-oxacyclo- and alpha-azacyclo-N-aziridinylimines: Effect of heteroatom and ring size in the ring expansion reaction

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Carbenes, generated from thermolysis of alpha-oxacyclo- and alpha-azacyclo-N-aziridinylimines in refluxing toluene, underwent ring expansions via insertion of alkyl carbenes into carbon-carbon bonds and intramolecular ammonium ylide formations, respectively. Ring expansion reaction of alpha-oxetanyl-N-aziridinylimines occurred via alkylidenecarbene intermediates, whereas thermal reaction of alpha-azetidinyl-N-aziridinylimines afforded alpha-aminoacetylene compounds via 1,2-H migration of alkylidenecarbene intermediates.
Publisher
GEORG THIEME VERLAG
Issue Date
2000-10
Language
English
Article Type
Article
Keywords

RADICAL CYCLIZATION; < 2,3> -SIGMATROPIC REARRANGEMENT; TRISUBSTITUTED OLEFINS; EFFICIENT SYNTHESIS; CATALYTIC METHODS; ALLYL COMPOUNDS; OXYGEN YLIDES; IMINES; ROUTE; GENERATION

Citation

SYNTHESIS-STUTTGART, pp.1622 - 1630

ISSN
0039-7881
URI
http://hdl.handle.net/10203/68412
Appears in Collection
CH-Journal Papers(저널논문)
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