Volume 22, Issue 39
Preparative Organic Chemistry
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ChemInform Abstract: Flash Vacuum Pyrolysis of Phenanthrene-3,4-dicarboxylic Anhydride and of Cyclobuta(c)phenanthrene-1,2-dione: Products of Ring Contraction, Insertion and Ring Cleavage.

M. ADENEY

M. ADENEY

Chem. Dep., Monash Univ., Clayton, Victoria 3168, Australia

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R. F. C. BROWN

R. F. C. BROWN

Chem. Dep., Monash Univ., Clayton, Victoria 3168, Australia

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K. J. COULSTON

K. J. COULSTON

Chem. Dep., Monash Univ., Clayton, Victoria 3168, Australia

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F. W. EASTWOOD

F. W. EASTWOOD

Chem. Dep., Monash Univ., Clayton, Victoria 3168, Australia

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I. W. JAMES

I. W. JAMES

Chem. Dep., Monash Univ., Clayton, Victoria 3168, Australia

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First published: October 1, 1991

Abstract

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ChemInform Abstract

Flash vacuum pyrolysis of both the title compounds (Ia) and (Ib) gives the same products (II)-(IV), the structures of the two ethynes of which are determined by independent syntheses. A mechanism is proposed which involves a reversible equilibrium between the intermediates (V) ( → (II)) and (VI) (→ (III) and (IV)).

chemical structure image

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