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Dimerization of Pyramidalized 3,4,8,9‐Tetramethyltetracyclo [4.4.0.0 3,9 .0 4,8 ]dec‐1(6)‐ene to a Hydrocarbon Featuring Four Cyclohexane Rings in Boat Conformations
Author(s) -
ReyCarrizo Matias,
BarniolXicota Marta,
FontBardia Mercè,
Vázquez Santiago
Publication year - 2014
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.201403985
Subject(s) - cyclobutane , cyclopentane , cyclohexane , alkene , dimer , chemistry , crystallography , hydrocarbon , ene reaction , ring (chemistry) , cyclohexene , stereochemistry , photochemistry , organic chemistry , catalysis
The synthesis, chemical trapping, and dimerization of a highly pyramidalized alkene is reported. Its dimer is a unique nonacycle featuring three planar cyclobutane rings, four cyclopentane rings, and four cyclohexane rings in boat conformations. The X‐ray diffraction analysis showed a H–H distance between the flagpole hydrogen atoms of 1.999 Å and a separation of 2.619 Å between the two flagpole carbon atoms. The three cyclobutane rings of the dimer were thermally stable.