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

Mark Sigalov; Zvi Rappoport

doi:10.1039/a703443a

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

Mark Sigalov, Zvi Rappoport

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

The crowded ketenes, (2,4,6-R₃C₆H₂)₂C=C=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.

Original language	English
Pages (from-to)	1911-1912
Number of pages	2
Journal	Journal of the Chemical Society. Perkin Transactions 2
Issue number	10
DOIs	https://doi.org/10.1039/a703443a
State	Published - 1 Jan 1997
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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

abstract = "The crowded ketenes, (2,4,6-R3C6H2)2C=C=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.",

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AU - Sigalov, Mark

AU - Rappoport, Zvi

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N2 - The crowded ketenes, (2,4,6-R3C6H2)2C=C=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.

AB - The crowded ketenes, (2,4,6-R3C6H2)2C=C=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.

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JF - Journal of the Chemical Society. Perkin Transactions 2

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

Abstract

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