Intramolecular 1,5- versus 1,6-hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrate models.
[reaction: see text] 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.
Francisco
Cosme G
CG
Instituto de Productos Naturales y Agrobiología del C.S.I.C. Carretera de La Esperanza 3, 38206 La Laguna, Tenerife, Spain.
Freire
Raimundo
R
Herrera
Antonio J
AJ
Peréz-Martín
Inés
I
Suárez
Ernesto
E
D002241:Carbohydrates / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular
D002241:Carbohydrates; D005609:Free Radicals; D007202:Indicators and Reagents; D006859:Hydrogen