Corannulene Subunit Acts as a Diene in a Cycloaddition Reaction: Synthesis of C80H32 Corannulyne Tetramer
Organic Letters2012Vol. 14(18), pp. 4942–4945
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Abstract
Distortion of six-membered rings in corannulene subunits of corannulyne (1,2-didehydrocorannulene) cyclotrimer activates the system for a cycloaddition reaction with another corannulyne unit. This unprecedented cycloaddition in which a corannulene fragment acts as a diene produces the largest oligomer of corannulyne reported to date. X-ray crystallography reveals the highly nonplanar structure of the tetramer which exhibits conformational and optical absorption properties very different from those of the cyclotrimer.
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