Regioselectivity in the Ring-Opening β-Scission of 2-Phenyl-1,3-dioxan-2-yl Radicals Derived from Bicyclic Benzylidene Acetals.

Regioselectivity in the ring opening of

Regioselectivity in the ring opening of 2-phenyl-1,3-dioxan-2-yl radicals derived from cyclic benzylidene acetals and comparison with deoxygenation of a carbohydrate diol via its cyclic thionocarbonate

✍ Brian P Roberts; Teika M Smits 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 107 KB

Ring-opening b-scission of monocyclic 2-phenyl-1,3-dioxan-2-yl radicals gives preferentially the more stabilised alkyl radical. However, analogous bicyclic radicals derived from two 4,6-O-benzylidene glucopyranosides afford primary radicals in preference to secondary radicals, a result that can be r