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) | Zendy

Vogel Emanuel | Zendy; Markowitz Gerd | Zendy; Schmalstieg Lutz | Zendy; Itô Shô | Zendy; Breuckmann Rolf | Zendy; Roth Wolfgang R. | Zendy

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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.

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