Product Class 3: S,S-acetals
Journal
Science of Synthesis
Journal Volume
2
Pages
369-381
Date Issued
2018
Author(s)
Luh T.-Y
Abstract
Compounds that have two sulfur atoms attached to the same carbon atom are known as dithioacetals and are discussed in this product class. The dithioacetal moiety was first described in 1885.[1] Nowadays, this functional group is frequently used as a protecting group for the carbonyl functionality (Scheme 1), because it can be prepared easily by the reaction of the carbonyl with the corresponding thiols.[2-5] Dithioacetals can be acyclic (Section 30.3.1) or cyclic (Sections 30.3.2, 30.3.3, 30.3.4, and 30.3.5). In general, the dithioacetal group is stable from pH 1 to pH 12. Depending on the structure of the substrates, and the nature of the reaction conditions, dithioacetals can be stable toward nucleophiles, organometallics, hydrides, and mild oxidizing reagents. Nevertheless, the carbonyl group can be readily regenerated from the dithioacetal under a range of different conditions, which have been described in both the literature and in Section 30.3.7.[2-5] ? 2018 Georg Thieme Verlag. All rights reserved.
Type
review