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Photochemistry of 9,10-Dicarbonyl-9,10-dihydroanthracene – A Source of 9,10-Dehydroanthracene?

✍ Scribed by Hans Henning Wenk; Wolfram Sander

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
116 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

9,10-Didehydroanthracene ( 1) is an interesting derivative of which is formed by monodecarbonylation of 2. Carbene 7 is labile towards visible-light irradiation and easily looses the p-benzyne that has been subject of several studies. In contrast to an earlier report, the photochemical second CO molecule to give 4. Carbene 7 and diyne 4 are characterized by IR and UV/Vis spectra, the IR spectra are decarbonylation of 9,10-dicarbonyl-9,10-dihydroanthracene (2) does not lead to 1 but rather to the ring-opened ene-diyne compared to calculations at the B3LYP/6-31G(d,p) level of theory.

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The reaction of 9-lithio-lo-ethyl-9,lO\_dihydroanthracene, J, with methyl iodide or ethyl bromide has been reported to give high yields of cis-9,lO dialkyl-9,10-dihydro-- anthracenes & DHA = dihydroanthracene]. 1'2 Only for reactions of 1 with carbon dioxide