Dithiane

Dithianes are heterocyclic compounds which comprise a cyclohexane structure, in which two methyl groups are replaced by sulfur atoms. There are three isomeric forms, the 1,2- dithiane, 1,3- dithiane and 1,4- dithiane the.

1,2- dithianes

1,2- dithianes form enantiomers due to the possible different dihedral angles of the sulfur -sulfur bond.

1.3 dithianes

1.3 dithianes are a good protecting group for carbonyl groups due to their inert behavior towards different synthesis conditions. They are formed in the reaction of the carbonyl compound with 1,3- propane thiol to form water. The protecting group, the mercury ( II) oxide can be removed with mercury compounds such as mercury (II ) chloride. Because of the very unpleasant odor of 1,3- propanethiol, alternative reagents for the formation of 1,3- dithianes have been developed. 1.3 dithianes were used in the total synthesis of natural products.

1.3 dithianes are used for example in the Corey -Seebach reaction as a protecting group for the reversal of carbonyl compounds with organolithium compounds such as butyllithium.

1,4- dithianes

1,4- dithianes can be obtained by reduction of 1,2 -ethanedithiol with metallic sodium, followed by reaction under suitable conditions with 1,2-dibromoethane. The main products, however, form polymeric structures. The thermal decomposition of these polymers also results in the formation of 1,4- dithiane.