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1997•Journal of the American Chemical SocietyRequires access

Corannulene. A Three-Step Synthesis 1

Lawrence T. Scott, Pei‐Chao Cheng, Mohammed M. Hashemi, Matthew S. Bratcher, Dayton T. Meyer, Hope B. Warren

Open publisher page 236 citations

Abstract

Thermal cyclization of 7,10-diethynylfluoranthene ( 3 ) in the gas phase gives corannulene ( 2 ), the smallest bowl-shaped polycyclic hydrocarbon fragment of C 60 with fullerene-like curvature. Bromocorannulene ( 10 ) and 1,6-dibromocorannulene ( 9 ) have also been obtained from flash pyrolysis of 7,10-bis(2,2-dibromovinyl)fluoranthene ( 8 ). Short, practical syntheses of several corannulene precursors from acenaphthenequinone are described which have made corannulene available in gram quantities.

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What this paper is about

Thermal cyclization of 7,10-diethynylfluoranthene ( 3 ) in the gas phase gives corannulene ( 2 ), the smallest bowl-shaped polycyclic hydrocarbon fragment of C 60 with fullerene-like curvature. Bromocorannulene ( 10 ) and 1,6-dibromocorannulene ( 9 ) have also been obtained from flash pyrolysis of 7,10-bis(2,2-dibromovinyl)fluoranthene ( 8 ). Short, practical syntheses of several corannulene precursors from acenaphthenequinone are described which have made corannulene available in gram quantities.

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OpenAlex reports 236 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

Thermal cyclization of 7,10-diethynylfluoranthene ( 3 ) in the gas phase gives corannulene ( 2 ), the smallest bowl-shaped polycyclic hydrocarbon fragment of C 60 with fullerene-like curvature. Bromocorannulene ( 10 ) and 1,6-dibromocorannulene ( 9 ) have also been obtained from flash pyrolysis of 7,10-bis(2,2-dibromovinyl)fluoranthene ( 8 ). Short, practical syntheses of several corannulene precursors from acenaphthenequinone are described which have made corannulene available in gram quantities.

Key concepts: Corannulene, Chemistry, Fullerene, Flash vacuum pyrolysis, Fluoranthene, Pyrolysis, Thermal decomposition, Hydrocarbon

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