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Synthesis 2000; 2000(11): 1622-1630
DOI: 10.1055/s-2000-7598
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Carbene Reactions of α-Oxacyclo- and α-Azacyclo-N-aziridinylimines: Effect of Heteroatom and Ring Size in the Ring Expansion Reaction

Sunggak Kim* , Joo-Yong Yoon
  • *Department of Chemistry and Center for Molecular Design and Synthesis, School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology, Taejon 305-701, Korea; Fax + 82 (42) 8 69 83 70; E-mail: skim@mail.kaist.ac.kr
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Publication Date:
31 December 2000 (online)

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Carbenes, generated from thermolysis of α-oxacyclo- and α-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 α-oxetanyl-N-aziridinylimines occurred via alkylidenecarbene intermediates, whereas thermal reaction of α-azetidinyl-N-aziridinylimines afforded α-aminoacetylene compounds via 1,2-H migration of alkylidenecarbene intermediates.

carbenes - heterocycles - hydrazones - ring expansions - ylides