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Tricyclo[6.2.0.0 3,6 ]deca‐1,3,6,8‐tetraene: A Remarkably Stable para ‐Quinodimethane from a Novel Rearrangement Reaction
Author(s) -
van Loon JanDirk,
Seiler Paul,
Diederich François
Publication year - 1993
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.199317061
Subject(s) - pericyclic reaction , cope rearrangement , toluene , deca , chemistry , cascade , medicinal chemistry , stereochemistry , organic chemistry , chromatography
Surprisingly, heating a solution of eyelobutane 1 in toluene afforded selectively the ( R,S ) stereoisomer of compound 2 . A cascade of pericyclic reactions is proposed to explain the formation of this remarkably stable para ‐quinodimethane, which was characterized by X‐ray crystallography.