Tosyl group: Difference between revisions

Revision as of 23:55, 9 February 2025

Chemical group derived from toluenesulfonic acid

Tosyl group

The tosyl group is a functional group in organic chemistry derived from p-toluenesulfonic acid. It is often abbreviated as Ts and is represented by the chemical formula _SO₂C₆H₄CH₃. The tosyl group is commonly used as a protecting group for alcohols and amines in organic synthesis.

Structure and properties

The tosyl group consists of a sulfonyl group (_SO₂_) attached to a phenyl group with a methyl group (_CH₃) at the para position. This structure imparts certain chemical properties, such as the ability to act as a good leaving group in nucleophilic substitution reactions. The presence of the sulfonyl group makes the tosyl group electron-withdrawing, which stabilizes the negative charge developed during the transition state of such reactions.

Applications in organic synthesis

Tosylates, the esters of tosyl groups, are widely used in organic synthesis. They are typically formed by the reaction of an alcohol with tosyl chloride in the presence of a base. The resulting tosylate can then undergo various substitution reactions, where the tosyl group acts as a leaving group.

Protecting group

In synthetic chemistry, the tosyl group is often used to protect alcohols and amines. The protection is achieved by converting the alcohol or amine into a tosylate, which can withstand various reaction conditions. The tosyl group can later be removed by reductive or hydrolytic methods to regenerate the original functional group.

Example: Tolterodine synthesis

An example of the use of tosyl groups in synthesis is the preparation of tolterodine, a medication used to treat urinary incontinence. In one of the steps, a tosylate intermediate is formed, which is then used in further reactions to build the final product.

Deprotection

The removal of the tosyl group, or deprotection, can be achieved through various methods. Commonly, the tosyl group is removed by treatment with strong acids or bases, or by using reducing agents such as lithium aluminum hydride.

Deprotection of a tosyl group

Related pages

References

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-'''Tosyl group''', also known as the '''tosylate group''', is a functional group in organic chemistry with the formula -SO<sub>2</sub>C<sub>6</sub>H<sub>4</sub>CH<sub>3</sub>. It is derived from toluenesulfonic acid and is often abbreviated as Ts or Tos. The tosyl group is commonly used as a protecting group for alcohols and amines, as well as a leaving group in nucleophilic substitution reactions.
+{{Short description|Chemical group derived from toluenesulfonic acid}}
+{{Use dmy dates|date=October 2023}}
-==Structure and Properties==
+== Tosyl group ==
-The tosyl group consists of a sulfonate (-SO<sub>2</sub>) connected to a methyl-substituted benzene ring. This structure imparts significant stability to the group, making it an excellent leaving group in various organic reactions. The tosylate anion (TsO<sup>−</sup>) is resonance-stabilized, which contributes to its stability and reactivity.
+The '''tosyl group''' is a functional group in organic chemistry derived from [[p-toluenesulfonic acid]]. It is often abbreviated as '''Ts''' and is represented by the chemical formula _SO<sub>2</sub>C<sub>6</sub>H<sub>4</sub>CH<sub>3</sub>. The tosyl group is commonly used as a protecting group for alcohols and amines in organic synthesis.
-==Synthesis==
+[[File:Tosylgruppe Strukturformel V.1.svg|thumb|right|200px|Structure of the tosyl group]]
-Tosyl groups are typically introduced into organic molecules through the reaction of an alcohol or amine with [[tosyl chloride]] (TsCl) in the presence of a base. The base, often triethylamine (Et<sub>3</sub>N), serves to neutralize the hydrochloric acid (HCl) byproduct.
-===For Alcohols===
+== Structure and properties ==
-{{Chem|ROH}} + TsCl + Et<sub>3</sub>N → {{Chem|ROTs}} + Et<sub>3</sub>N·HCl
+The tosyl group consists of a [[sulfonyl group]] (_SO<sub>2</sub>_) attached to a [[phenyl group]] with a [[methyl group]] (_CH<sub>3</sub>) at the para position. This structure imparts certain chemical properties, such as the ability to act as a good leaving group in nucleophilic substitution reactions. The presence of the sulfonyl group makes the tosyl group electron-withdrawing, which stabilizes the negative charge developed during the transition state of such reactions.
-===For Amines===
+== Applications in organic synthesis ==
-{{Chem|R<sub>2</sub>NH}} + TsCl + Et<sub>3</sub>N → {{Chem|R<sub>2</sub>NTs}} + Et<sub>3</sub>N·HCl
+Tosylates, the esters of tosyl groups, are widely used in organic synthesis. They are typically formed by the reaction of an alcohol with [[tosyl chloride]] in the presence of a base. The resulting tosylate can then undergo various substitution reactions, where the tosyl group acts as a leaving group.
-==Applications==
+[[File:Tosylat-Struktur.svg|thumb|right|200px|Structure of a tosylate group]]
-===Protecting Groups===
-The tosyl group is widely used as a protecting group for alcohols and amines during synthetic procedures. Protected alcohols and amines are less reactive and can withstand conditions that would otherwise cause them to react. This allows for selective reactions to be carried out on other parts of the molecule.
-===Leaving Group===
+=== Protecting group ===
-Due to its stability, the tosyl group is an excellent leaving group for nucleophilic substitution reactions, including [[S_N1]] and [[S_N2]] mechanisms. This property is particularly useful in the synthesis of ethers, esters, and other compounds.
+In synthetic chemistry, the tosyl group is often used to protect alcohols and amines. The protection is achieved by converting the alcohol or amine into a tosylate, which can withstand various reaction conditions. The tosyl group can later be removed by reductive or hydrolytic methods to regenerate the original functional group.
-==Removal==
+[[File:Ts group.png|thumb|right|200px|Tosyl group as a protecting group]]
-The tosyl protecting group can be removed under acidic or basic conditions, depending on the substrate and the desired outcome. For example, tosyl-protected alcohols can be deprotected with hydrochloric acid (HCl) in water.
-==Safety==
+=== Example: Tolterodine synthesis ===
-Tosyl chloride, used in the synthesis of tosyl groups, is corrosive and should be handled with care. It can cause severe burns to the skin and eyes and should be used in a fume hood with appropriate personal protective equipment.
+An example of the use of tosyl groups in synthesis is the preparation of [[tolterodine]], a medication used to treat urinary incontinence. In one of the steps, a tosylate intermediate is formed, which is then used in further reactions to build the final product.
-==See Also==
+[[File:Tolterodine Synthesis.png|thumb|right|200px|Synthesis of tolterodine involving tosylate intermediates]]
+== Deprotection ==
+The removal of the tosyl group, or deprotection, can be achieved through various methods. Commonly, the tosyl group is removed by treatment with strong acids or bases, or by using reducing agents such as [[lithium aluminum hydride]].
+[[File:Ts deprotect.png|thumb|right|200px|Deprotection of a tosyl group]]
+== Related pages ==
+* [[Sulfonyl group]]
 * [[Protecting group]]
-* [[Leaving group]]
-* [[Tosyl chloride]]
 * [[Nucleophilic substitution]]
-* [[Sulfonate]]
-[[Category:Organic chemistry]]
+== References ==
+{{Reflist}}
 [[Category:Functional groups]]
+[[Category:Protecting groups]]
-{{Chemistry-stub}}