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

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journal contribution
posted on 04.05.2002, 00:00 by Cosme G. Francisco, Raimundo Freire, Antonio J. Herrera, Inés Peréz-Martín, Ernesto Suárez
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.