Download PDF
Synthesis 2000; 2000(11): 1622-1630
DOI: 10.1055/s-2000-7598
feature article
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >