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Intramolecular 1,5- versus 1,6-Hydrogen Abstraction Reaction Promoted by Alkoxy Radicals in Carbohydrate Models

2002; American Chemical Society; Volume: 4; Issue: 11 Linguagem: Inglês

10.1021/ol025981u

1523-7060

Cosme G. Francisco, Raimundo Freire, Antonio J. Herrera, Inés Pérez‐Martín, Ernesto Suárez,

Oxidative Organic Chemistry Reactions

The alkoxy radical generated by reaction of 3,7-anhydro-2-deoxyoctitols with (diacetoxyiodo)benzene (DIB) and iodine abstracts regioselectively either the proton at C7 or that at C4 depending on the electronegativity of the substituent at C4. The correct election of this substituent can switch the reaction to give 2,9-dioxabicyclo[3.3.1]nonane or hexahydro-2H-furo[3,2-b]pyran ring systems.