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Photoadditionen von Dibenz[ a , c ]‐ und Dibenz[ a , h ]anthracen an Cyclopentadien
Author(s) -
Kaupp Gerd,
Grüter HeinzWilli
Publication year - 1980
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19801130442
Subject(s) - chemistry , cyclopentadiene , anthracene , adduct , medicinal chemistry , photochemistry , stereochemistry , organic chemistry , catalysis
Photoadditions of Dibenz[ a , c ]‐ and Dibenz[ a , h ]anthracene to Cyclopentadiene The electronically excited carcinogens and mutagens 1 and 5 react with cyclopentadiene ( 2 ) at 0°C to give the stereochemically well defined [4 + 2]‐ ( 3 ) and [4 + 4]‐ ( 4 ) or [4 + 2]‐ ( 6 ) and [2 + 4]‐adducts ( 7 ), resp. The products are characterized by UV, fluorescence, and 1 H NMR spectra which reveal transannular interactions. 4 gives the cage compound 10 on photolysis.