Abstract
Publisher Summary This chapter discusses the relative reactivities of hydroxyl groups in carbohydrates, which is of considerable value in the field of syntheses. The selective reactivity of hydroxyl groups of carbohydrates in many instances seems to be a consequence of spatial arrangement of the groups. This is especially indicated in those reactions, such as acyl migration, where the postulation of a cyclic intermediate seems to explain the course of the reaction. Neighboring groups in general may have a very pronounced effect on the reactivity of a given hydroxyl group. The enhanced reactivity of the 2-hydroxyl as compared to other secondary hydroxyl groups has been noted primarily in reactions requiring alkaline media. This effect is probably a result of the greater acidity of hydroxyl groups adjacent to a carbonyl or a potential carbonyl group. The greater reactivity of the primary and the 2-hydroxyl group over those of the other secondary alcohol groups is strongly indicated.
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