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Thermal Deoxygenation of syn ‐15, 16‐Dioxo‐1,6 : 8,13‐bismethano[14]annulene to the Pyrene Isomer Dicyclohepta[ cd,gh ]pentalene (Azuleno[2,1,8‐ ija ]azulene)
Author(s) -
Vogel Emanuel,
Markowitz Gerd,
Schmalstieg Lutz,
Itô Shô,
Breuckmann Rolf,
Roth Wolfgang R.
Publication year - 1984
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.198407191
Subject(s) - deoxygenation , annulene , chemistry , pentalene , photochemistry , pyrene , anthracene , phosphole , thermal decomposition , thiophene , singlet oxygen , medicinal chemistry , double bond , stereochemistry , oxygen , organic chemistry , molecule , catalysis
A unique reaction takes place in the pyrolysis of the diketone 1 . The formation of the pyrene isomer 2 (60%) can hardly be explained other than in terms of via a 1,2‐dioxetane; thus, this reaction would be the reverse of the oxidative cleavage of electron‐rich double bonds with singlet oxygen. In addition, 30% anthracene is obtained by the expected stepwise decomposition of 1 via a norcaradienone derivative.