Exploring modular domino reactions: competing processes based on the nature of the angular substituent.
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.
Elkhayat
Zobida
Z
Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Gif-sur-Yvette, France.
Safir
Imad
I
Retailleau
Pascal
P
Arseniyadis
Siméon
S
D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction
D006571:Heterocyclic Compounds