Issue 10, 1997

Intramolecular cyclization of bis(2,4,6-trialkylphenyl) ketenes to isochromenes

Abstract

The crowded ketenes, (2,4,6-R3C6H2)2C[double bond, length half m-dash]C[double bond, length half m-dash]O, R = Pri, Me, undergo intramolecular cyclization of the ketene oxygen on an o-alkyl group to give substituted isochromenes. The reaction is two orders of magnitude faster at 170 °C for R = Pri than for R = Me. A stepwise reaction involving a 1,5-sigmatropic rearrangement to a conjugated tetraenal which does not accumulate and rapidly cyclizes to the isochromene is suggested.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1997, 1911-1912

Intramolecular cyclization of bis(2,4,6-trialkylphenyl) ketenes to isochromenes

M. Sigalov and Z. Rappoport, J. Chem. Soc., Perkin Trans. 2, 1997, 1911 DOI: 10.1039/A703443A

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