Three Benzynes and the Ynolate

Key words

triptycenes - arynes - ynolates

Significance

The triptycene structure is a remarkable scaffold that is frequently employed in functional materials as a result of its three dimensional, noncompliant structures and the interstitial space around the molecule. Most syntheses are based on a Diels–Alder cycloaddition between anthracene and an aryne. The authors describe a one-pot synthesis of triptycenes that proceeds through three cycloadditions of arynes to ­ynolates.

 

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Comment

The approach of formally inserting three arynes into an alkyne is a new and powerful way to obtain both simple and substituted triptycenes. Calculations provide an insight into the mechanism and explain the high regioselectivity (head-to-head-to-head).

 

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