International Summer School PROGRAM - Laboratoire d'Infochimie ...
International Summer School PROGRAM - Laboratoire d'Infochimie ...
International Summer School PROGRAM - Laboratoire d'Infochimie ...
Create successful ePaper yourself
Turn your PDF publications into a flip-book with our unique Google optimized e-Paper software.
A Facile Palladium-Mediated Contractions of Benzene to<br />
Cyclopentadiene: Transformations of Palladium(II) p-Benziporphyrin<br />
Bartosz Szyszko, Lechosław Latos-Grażyński and Ludmiła Szterenberg<br />
Department od Chemistry<br />
University of Wrocław<br />
14 F. Joliot-Curie St., 50-383 Wrocław, Poland<br />
Palladium(II) p-benziporphyrin provides the unique macrocyclic vessel to afford the<br />
contraction of benzene to cyclopentadiene embedded in the first instance of 21carbaporphyrin<br />
complexes. Addition of palladium(II) and a hydroxide ion to a C–C<br />
double bond, β elimination, and competing cheletropic extrusion of carbon oxide and<br />
1,2-hydride shift reactions lead to the contraction of p-phenylene to form a<br />
cyclopentadiene unit. This reaction results in the formation of a 21-carbaporphyrin from<br />
a palladium(II) p-benziporphyrin. In the case of chloropalladium 1,4-naphthiporphyrin<br />
similar reactivity pattern allowed to obtain 21-benzocarbaporphyrin on the course of<br />
naphthalene to isoindene contraction.