Journal of Organic Chemistry p. 1351 - 1353 (1994)
Update date:2022-08-03
Topics:
Pu, Lin
Grubbs, Robert H.
New syntheses of both substituted and unsubstituted benzobarrelenes are described.Treatment of 3,5-cyclohexadiene-cis-1,2-diol with benzaldehyde dimethyl acetal in the presence of a catalytic amount of p-toluenesulfonic acid gave 1,2-(benzylidenedioxy)-3,5-cyclohexadiene (2).Addition of benzynes to 2 provided 3 and 4.Treatment of 3 and 4 with excess LDA and potassium tert-butoxide afforded benzobarrelenes 1 and 5 in good yields.
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