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Light-Induced Coumarin Cyclopentannelation

2005; American Chemical Society; Volume: 7; Issue: 23 Linguagem: Inglês

10.1021/ol051952i

1523-7060

Marko Soltau, Maren Göwert, Paul Margaretha,

Fluorine in Organic Chemistry

[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.