Alkylation

Generally alkylating (alkyl or alkylation) is the generic name of the chemical reaction to introduce an alkyl group into a compound by substitution reaction or an addition reaction [¹]. I include the reaction that an alkyl group is substituted for as a reaction form in a wide sense.

Various chemical reactions are used for alkylation, but a characteristic and limits are different, and there is not the alkylation reaction that I can use for all scenes in each. I explain below a representative alkylation reaction.

Table of contents

求電子置換反応 for the heteroatom

It is a reaction to introduce an alkyl group into on the heteroatom with alkyl having the elimination group including the alkyl halide. It becomes the nucleophilic substitution of the heteroatom for the introduced alkyl group. 〉 which knows a lot about 〈 article nucleophilic substitution

${\displaystyle {\rm {CH_{3}CH_{2}SH+CH_{3}I\longrightarrow CH_{3}CH_{2}SCH_{3}}}}$ 

Addition reaction for the unsaturated bond

 

Alkylation with the Grignard reagent

A reaction to alkylate for carbon - carbon or carbon - heteroatom unsaturated bond by the reaction by various ion reactions or the radical reaction is known.

For example, representatives include an alkylation reaction to carbonyl carbon with the Grignard reagent.

求電子置換反応

Alkylation is possible like Friedel-Crafts reaction with the aromatic compounds by 求電子置換反応.

Methylation with the diazomethane

Generally, the methyl esterification is exchange reaction of the alcohol ingredient, and methyl esterification with the applicable しなが diazomethane is an alkylation reaction by 求電子置換 for hydroxy oxygen for alkylation.

Radical reaction

The correction of this knob is expected.

Carbene reaction

The correction of this knob is expected.

Other alkylating

Alkylation is possible by the ように reaction method not to correspond to substitution reaction or an addition reaction mechanically as follows. Because a reaction is formal, and these methods are equivalent to substitution in a wide sense, I may include it in alkylation.

Reductive alkylating of amine

An alkyl group is replaced amine and carbonyl compounds with for amine by one pot composition by generation of the azomethine and its reduction. I may call this reductive amination reaction reductive alkylation of amine.

Alkylating agent in the medical care

Nitrogen mustard

• Cyclophosphamide
• Ifosfamide
• Melphalan

Nitrosourea

• Nimustine
• Ranimustine
• Carmustine

Imidazo tetragin derivative

• Temozolomide (TMZ, テモダール ®)

Footnote

[Help]

1. The dehydration condensation reaction of ^ carboxylic acid and the alcohol is alkyl substitution of hydrogen carboxylic acid formally, but reaction classes are different and do not correspond.

Source

• Hiroo Tominaga, Shuji Tomota "alkylation" "world size encyclopedia" CD-ROM version, Heibonsha Publishers Ltd., 1998.
• The fifth edition Saburo Nagakura others (編) "alkylation" "Iwanami physics and chemistry dictionary" CD-ROM version, Iwanami Shoten, 1998.

Allied item

• Chemical reaction
• Methylate

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