The Journal of Organic Chemistry

Conversion of 1-isopropylidene-4, 4-dimethyl-2, 5-cyclohexadiene to its crisscross dimer

SF Nelsen, MF Teasley

Index: Nelsen, Stephen F.; Teasley, Mark F. Journal of Organic Chemistry, 1989 ,  vol. 54,  # 11  p. 2667 - 2674

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Citation Number: 7

Abstract

The title compound, 1, gives only aromatization to 6 and polymerization upon treatment with acid in methylene chloride or when TFAA or TFA are added separately to the reaction mixture. When both TFAA and TFA are present at low temperatures, HBF,. EhO causes remarkably efficient formation of the crisscross dimer 2, which is isolated in up to 80% yield. Ozonolysis of 2 gives the diepoxide or rearranged compounds containing acetyl groups. ...