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Nickel‐Catalyzed Cyclodimerization of Hexapentaenes: [4]Radialenes and [5]Radialenones with Cumulated Double Bonds
Author(s) -
Iyoda Masahiko,
Kuwatani Yoshiyuki,
Oda Masaji,
Kai Yasushi,
Kaneshisa Nobuko,
Kasai Nobutami
Publication year - 1990
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.199010621
Subject(s) - cyclopentanone , steric effects , alkyl , double bond , catalysis , nickel , chemistry , ring (chemistry) , polymer chemistry , medicinal chemistry , stereochemistry , photochemistry , organic chemistry
The size of the alkyl substituents of [5]cumulenes such as 1 governs their nickelcatalyzed cyclodimerization. The sterically encumbered compound 1 affords the radialenone 2 and the radialene 3 . Head‐to‐tail coupling is observed for smaller substituents. The cyclopentanone ring in 2 is nearly planar.