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Two Novel Thermal Biradical Cyclizations of Enyne‐Ketenimines: Theory, Experiment, and Synthetic Potential
Author(s) -
Schmittel Michael,
Steffen JensPeter,
Wencesla Ángel Miguel Á.,
Engels Bernd,
Lennartz Christian,
Hanrath Michael
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980619)37:11<1562::aid-anie1562>3.0.co;2-h
Subject(s) - enyne , substituent , alkyne , chemistry , ring (chemistry) , computational chemistry , stereochemistry , photochemistry , organic chemistry , catalysis
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 R 1 at the alkyne terminus.