Formal [4 + 4] cycloaddition of 3-arylcyclobutanones with Anthracene (cas 120-12-7) and their acid-promoted intramolecular cyclization with skeletal rearrangement

Add time:08/28/2019    Source:sciencedirect.com

A reaction of 3-arylcyclobutanones with Anthracene (cas 120-12-7) in the presence of TiCl4 gave 14-aryl-9,10-dihydro-9,10-butanoanthracen-12-ones as a formal [4 + 4] cycloadduct of anthracenes with a C4 unit formed by cleaving the more substituted C2C3 bond of cyclobutanones. On the other hand, activation of 3-arylcyclobutanones with TfOH in the absence of nucleophiles gave 2-tetralones with skeletal rearrangement.

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