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Highly Regioselective Solid-State Photodimerization of Naphthoquinolizinium Salts

✍ Scribed by Heiko Ihmels; Christian J. Mohrschladt; Andreas Schmitt; Milena Bressanini; Dirk Leusser; Dietmar Stalke

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
191 KB
Volume
2002
Category
Article
ISSN
1434-193X

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✦ Synopsis

The photodimerization of benzo-annellated acridizinium derivatives, namely naphtho[1,2-b]quinolizinium and naphtho[2,1-b]quinolizinium bromide, has been investigated in solution and in the solid state. Irradiation of the naphthoquinolizinium salts in solution gave all possible regioisomers in an unselective [4+4] photocycloaddition reaction. In contrast, the irradiation of crystalline samples resulted in regioselective dimerization to give the anti-head-to-tail photodimers.

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