G. Chittenden
Dec 15, 1980
Citations
0
Influential Citations
23
Citations
Journal
Carbohydrate Research
Abstract
Abstract Isopropylidenation of d -mannitol ( 2 ) under neutral conditions, by treatment with 2,2-dimethoxypropane in 1,2-dimethoxyethane, is described. 1,2,:5,6-Di- O -isopropylidene- d -mannitol is the main equilibrium product, which does not undergo further subtitution under the conditions used. 1,2:3,4:5,6-Tri- O -isopropylidene- d -mannitol, the other major product, was shown to be derived mainly from initial 3,4-substitution of 2 . The presence of a difunctional ether, of suitable geometry, is a necessary requirement for the reaction. Some mechanistic aspects of the reaction are discussed.