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A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two
Typically, in organic synthesis, ketones and aldehydes are protected as their
Corey-Seebach Reaction
methylene bridge
In organic chemistry, a methylene bridge, methylene spacer, or methanediyl group is any part of a molecule with formula ; namely, a carbon atom bound to two hydrogen atoms and connected by single bonds to two other distinct atoms in the rest of t ...
s (-- units) are replaced by sulfur centres. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane.
1,3-Dithianes
1,3-Dithianes are protecting group of somecarbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containi ...
-containing compounds due to their inertness to many conditions. They form by treatment of the carbonyl compound with 1,3-propanedithiol
1,3-Propanedithiol is the chemical compound with the formula HSCH2CH2CH2SH. This dithiol is a useful reagent in organic synthesis. This liquid, which is readily available commercially, has an intense stench.
Use in organic synthesis
1,3-Propan ...
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 also employed in umpolung
In organic chemistry, umpolung () or polarity inversion is the chemical modification of a functional group with the aim of the reversal of polarity of that group. This modification allows secondary reactions of this functional group that would ot ...
reactions, such as the Corey–Seebach reaction
The Corey–Seebach reaction, or Seebach Umpolung is a name reaction of organic chemistry that allows for acylation by converting aldehydes into lithiated 1,3-dithianes. The lithiated 1,3-dithianes serves as an acyl anion equivalent, undergoing a ...
:T. W. Green, P. G. M. Wuts, "Protective Groups in Organic Synthesis" Wiley-Interscience, New York, 1999. .
:
Typically, in organic synthesis, ketones and aldehydes are protected as their dioxolane
Dioxolane is a heterocyclic acetal with the chemical formula (CH2)2O2CH2. It is related to tetrahydrofuran by interchange of one oxygen for a CH2 group. The corresponding saturated 6-membered C4O2 rings are called dioxanes. The isomeric 1,2-diox ...
s instead of dithianes.
References
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Corey-Seebach Reaction