Two Novel Thermal Biradical Cyclizations of Enyne-Ketenimines: Theory, Experiment, and Synthetic Potential

Both benzocarbazoles and quinolines can be synthesized from enyne ketenimines 1 generated in situ via biradical intermediates (see reaction below). Which of the heterocyclic ring systems is formed depends on the choice of the substituent R1 at the alkyne terminus.

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 1998-06, Vol.37 (11), p.1562-1564
Main Authors: Schmittel, Michael, Steffen, Jens-Peter, Wencesla Ángel, Miguel Á., Engels, Bernd, Lennartz, Christian, Hanrath, Michael
Format: Article
Language:English
Subjects:
Cycloaromatizations
Diradicals
Enynes
Ketenimines
Quantum-chemical calculations
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Both benzocarbazoles and quinolines can be synthesized from enyne ketenimines 1 generated in situ via biradical intermediates (see reaction below). Which of the heterocyclic ring systems is formed depends on the choice of the substituent R1 at the alkyne terminus.
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19980619)37:11<1562::AID-ANIE1562>3.0.CO;2-H