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Selective Synthesis of Fused Cyclooctatetraenes by [4+4] Coupling Between Two Different Diene Units
Author(s) -
Yamamoto Yoshihiko,
Ohno Tatsuya,
Itoh Kenji
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20021018)8:20<4734::aid-chem4734>3.0.co;2-b
Subject(s) - cyclopentane , reactivity (psychology) , moiety , diene , ring (chemistry) , cyclohexane , derivative (finance) , chemistry , coupling (piping) , medicinal chemistry , stereochemistry , materials science , organic chemistry , medicine , natural rubber , alternative medicine , pathology , financial economics , economics , metallurgy
In the presence of CuCl and 1,3‐dimethyl‐3,4,5,6‐tetrahydro‐2(1 H )‐pyrimidinone, the [4+4] coupling between zirconacyclopentadienes and 1,3‐diiodobutadienes fused through an oxygen or nitrogen five‐membered ring proceeded at ambient temperature to afford fully substituted polycyclic cyclooctatetraenes in good yields. The fused ring moiety of the diiodides plays a critical role. The corresponding acyclic diiodide and a cyclohexane‐fused analogue gave no coupling product, and a cyclopentane derivative showed only moderate reactivity. Correlation of the structures of the diiodides and their reactivity was established by an X‐ray and density functional study.