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Mechanistic Aspects of the Palladiun‐Catalyzed Cyclization of 5‐Methylenecyclooctene
Author(s) -
Heumann Andreas,
Reglier Marius,
Waegell Bernard
Publication year - 1979
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197908671
Subject(s) - catalysis , bicyclic molecule , benzene , chemistry , organic chemistry , medicinal chemistry , combinatorial chemistry
An insight into the course of the Pd‐catalyzed oxidation of diolefins is provided by reaction of 5‐methylenecyclooctene (1) with PdCl 2 /CuCl 2 /HOAc/NaOAc to give the bicyclic compounds (2) to (5) . In benzene, the diolefin (1) reacts with Pd(PhCN) 2 Cl 2 to form the isolable σ‐π complex (6) which cyclizes in hitherto unexplained manner to compounds (2) to (5) .