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Exploring modular domino reactions: competing processes based on the nature of the angular substituent
Zobida Elkhayat1, Imad Safir, Pascal Retailleau
1Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Gif-sur-Yvette, France.
Abstract:
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 pi-system and the length of the methylene spacer at the angular position.
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