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Exploring Modular Domino Reactions:  Competing Processes Based on the Nature of the Angular Substituent

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journal contribution
posted on 08.11.2007, 00:00 authored by Zobida Elkhayat, Imad Safir, Pascal Retailleau, Siméon Arseniyadis
The octaline diol system 6 was found to undergo an interesting set of reactions upon treatment with PhI(OAc)2, leading, in a single synthetic operation, to complex oxygen heterocycles. Experimental evidence supports an intramolecular hetero[4 + 2 + 2] adduct that has heretofore never been observed, which completely dominates the hetero[4 + 2] path in several cases. The domino protocol can be biased one way or another depending on both the nature of the π-system and the length of the methylene spacer at the angular position.