• Source: Dithiane

A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges (-CH2- units) are replaced by sulfur. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane. They are all colorless solids.




1,2-Dithianes


1,2-Dithiane is an organosulfur compound with the formula S2C4H8. It is one of three isomers of the formula (CH2)4S2. The 1,2-isomer, a disulfide, arises by the oxidation of 1,4-butanedithiol.




1,3-Dithianes


1,3-Dithiane is an organosulfur compound with the formula CH2S2C3H6. It is one of three isomers of the formula (CH2)4S2. The 1,3-isomer arises by the reaction of 1,3-propanedithiol with formaldehyde.
1,3-Dithianes are sometimes used as protecting group of carbonyl-containing compounds. They form by treatment of the carbonyl compound with 1,3-propanedithiol under conditions that remove water from the system. The protecting group can be removed with mercuric reagents, a process that exploits the high affinity of Hg(II) for thiolates. 1,3-Dithianes are more importantly employed in umpolung reactions, such as the Corey–Seebach reaction:




1,4-Dithianes


1,4-Dithiane is an organosulfur compound with the formula (SC2H4)2. It is one of three isomers of the formula (CH2)4S2. The 1,4-isomer, a bisthioether, arises by the alkylation of 1,2-ethanedithiol with 1,2-dibromoethane. It has no applications but traces occur as a product of degradations, e.g., cooking coal pyrolysis.




References






External links


Corey-Seebach Reaction
1,3-Dithianes, 1,3-Dithiolanes

Kata Kunci Pencarian:

• Tiana (kimia)
• Dithiane
• Umpolung
• Corey–Seebach reaction
• Propane-1,3-dithiol
• 2,5-Undecanedione
• Elias James Corey
• N-Butyllithium
• Cyanide poisoning
• Heterocyclic compound
• Cyclobutanone