Light-induced coumarin cyclopentannelation.
[reaction: see text] Whereas cyclopentenylcarbenes resulting from photocycloaddition of 4-alk-1-ynylcoumarins to 2,3-dimethylbut-2-ene undergo tandem cyclization to hitherto unknown tetracyclic (4-hetera)cyclopent[b,c]acenaphthylenes, the corresponding cyclopentenylnitrenes stemming from 4-cyanocoumarins and the same alkene are converted into tricyclic imines via H-abstraction.
Soltau
Marko
M
Institute of Organic Chemistry, University of Hamburg, D-20146 Hamburg, Germany.
Göwert
Maren
M
Margaretha
Paul
P
D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D003374:Coumarins / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D008027:Light; D015394:Molecular Structure
D000475:Alkenes; D003374:Coumarins; D003517:Cyclopentanes; D007097:Imines