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 …

E Vogel, G Markowitz, L Schmalstieg…

Index: Vogel, Emanuel; Markowitz, Gerd; Schmalstieg, Lutz; Ito, Sho; Breuckmann, Rolf; Roth, Wolfgang R. Angewandte Chemie, 1984 , vol. 96, # 9 p. 719 - 720

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Citation Number: 3

Abstract

The lox-arene 1 l-oxo-1, 6-methano [l0] annulene 1 [11 is stable up to ca. 200 C. Above this temperature, it undergoes quantitative decarbonylation to yield naphthalene 3, a reaction which in the gas phase is found to have the activation parameters E,= 35.6 k 0.1 kcal/mol and A=(7.2 k 0.7) x 10I3 sI. The relatively high thermal stability of 1 ['] can be rationalized if one assumes that the de-