A Facile Palladium‐Mediated Contraction of Benzene to Cyclopentadiene: Transformations of Palladium(II)  p ‐Benziporphyrin | Zendy

Szyszko Bartosz | Zendy; LatosGrażyński Lechosław | Zendy; Szterenberg Ludmiła | Zendy

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A Facile Palladium‐Mediated Contraction of Benzene to Cyclopentadiene: Transformations of Palladium(II) p ‐Benziporphyrin

Author(s) -

Szyszko Bartosz,

LatosGrażyński Lechosław,

Szterenberg Ludmiła

Publication year - 2011

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201102218

Subject(s) - palladium , cyclopentadiene , chemistry , benzene , hydroxide , contraction (grammar) , hydride , photochemistry , medicinal chemistry , polymer chemistry , inorganic chemistry , organic chemistry , catalysis , hydrogen , medicine

Feeling the contractions : Addition of palladium(II) and a hydroxide ion to a C–C double bond, β elimination, and competing cheletropic extrusion of carbon oxide and 1,2‐hydride shift reactions lead to the contraction of p ‐phenylene to form a cyclopentadiene unit. This reaction results in the formation of a 21‐carbaporphyrin from a palladium(II) p ‐benziporphyrin (see picture; C red/gray, N blue, Pd orange).

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