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Photochemistry of 9,10‐Dicarbonyl‐9,10‐dihydroanthracene – A Source of 9,10‐Dehydroanthracene?
Author(s) -
Wenk Hans Henning,
Sander Wolfram
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199901)1999:1<57::aid-ejoc57>3.0.co;2-s
Subject(s) - chemistry , carbene , decarbonylation , aryne , photochemistry , ring (chemistry) , medicinal chemistry , molecule , derivative (finance) , organic chemistry , catalysis , financial economics , economics
9,10‐Didehydroanthracene ( 1 ) is an interesting derivative of p ‐benzyne that has been subject of several studies. In contrast to an earlier report, the photochemical decarbonylation of 9,10‐dicarbonyl‐9,10‐dihydroanthracene ( 2 ) does not lead to 1 but rather to the ring‐opened ene‐diyne 4 . The key intermediate for this reaction is keto carbene 7 which is formed by monodecarbonylation of 2 . Carbene 7 is labile towards visible‐light irradiation and easily looses the second CO molecule to give 4 . Carbene 7 and diyne 4 are characterized by IR and UV/Vis spectra, the IR spectra are compared to calculations at the B3LYP/6‐31G(d,p) level of theory.