Premium
Thermal and photochemical reactions of naphtho[1,2,3,4‐ def ]chrysene with 4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione
Author(s) -
Angermund Klaus,
Bunte Reinhard,
Goddard Richard,
Leitich Johannes,
Polansky Oskar E.,
Zander Maximilian
Publication year - 1988
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.19881210917
Subject(s) - chrysene , chemistry , cycloaddition , yield (engineering) , photochemistry , quantum yield , medicinal chemistry , hydrogen , organic chemistry , fluorescence , catalysis , anthracene , materials science , physics , quantum mechanics , metallurgy
The thermal and photochemical reactions between naphtho‐[1,2,3,4‐ def ]chrysene ( 1 ) and 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione ( 2 ) have been compared. In the thermal reaction, 2 electrophilically attacks 1 to give substitution product 4 which in part is further transformed into 5 and 6 . In the light‐induced reaction, 2 predominantly undergoes [4π + 2π] cycloaddition to 1 with subsequent loss of hydrogen to yield 6 which then photodecomposes to give a complex mixture containing 10. 5 exists in two atropisomeric forms. The structure of one form, 5b , was determined by X‐ray crystallography.