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A Highly Efficient Triplet Analogue of a Thermal Biradical Cyclization—The Photochemical C 2 –C 6 Cyclization of Enyne‐Heteroallenes
Author(s) -
Schmittel Michael,
Rodríguez David,
Steffen JensPeter
Publication year - 2000
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 - 10.1002/1521-3773(20000616)39:12<2152::aid-anie2152>3.0.co;2-4
Subject(s) - enyne , chemistry , yield (engineering) , photochemistry , combinatorial chemistry , organic chemistry , physics , catalysis , thermodynamics
In a high yield photoreaction (90–99 %), enyne–carbodiimides (X=N) cyclize to indoloquinolines within a few minutes (see scheme). Analogously, enyne–ketenimines (X=CAr) photocyclize to benzocarbazoles, which paves the way to a simple synthesis of certain photoactive prodrugs.