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

Mark Sigalov, Zvi Rappoport

Research output: Contribution to journalArticlepeer-review

5 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 languageEnglish
Pages (from-to)1911-1912
Number of pages2
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number10
DOIs
StatePublished - 1 Jan 1997
Externally publishedYes

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