Claisen rearrangement reaction

In 1912, German chemist Rainer Ludwig Claisen published the rearrangement of allyl phenyl ethers to their corresponding C-allyl phenols, as well as the conversion of the O-allylated acetoacetic ester to its C-allylated isomer upon treatment with ammonium chloride, followed by distillation. The thermal rearrangement of allyl vinyl ethers to their corresponding γ,δ-unsaturated carbonyl compounds has since been known as the Claisen rearrangement.

The precursor allyl vinyl ethers can be prepared in several ways, such as from the allylic alcohols via mercuric ion-catalyzed exchange with ethyl vinyl ether, or by Wittig olefination of allyl formates and carbonyl compounds.

A modification is the Johnson-Claisen rearrangement, in which an allylic alcohol is heated with trialkyl orthoacetate under mildly acidic conditions to produce a γ,δ-unsaturated ester.

The Claisen rearrangement has been used in many successful total synthesis campaigns, including K.C. Nicolaou and colleagues' synthesis of 1-O-methylforbesione via tandem Claisen rearrangement/Diels-Alder reactions.

Review available Thermo Scientific products for the Claisen rearrangement reaction:

N.° de Catálogo Nombre Tamaño Precio (EUR) Cantidad
A11766.30 Allyl bromide, 99%, stab. with 300-1000ppm Propylene oxide Each
33,84

Precio exclusivo en nuestra web

42,30
Ahorro 8,46 (20%)
L06004.AP Triethyl orthoacetate, 97% Each
90,10

Precio exclusivo en nuestra web

106,00
Ahorro 15,90 (15%)
A15000.30 Ammonium chloride, 98+% Each
22,10

Precio exclusivo en nuestra web

26,00
Ahorro 3,90 (15%)
A15691.AK Ethyl vinyl ether, 99%, stab. Each
27,29

Precio exclusivo en nuestra web

32,10
Ahorro 4,81 (15%)
L06004.AE Triethyl orthoacetate, 97% Each
26,44

Precio exclusivo en nuestra web

31,10
Ahorro 4,66 (15%)
A15000.0B Ammonium chloride, 98+% Each
42,08

Precio exclusivo en nuestra web

49,50
Ahorro 7,42 (15%)
A15691.AP Ethyl vinyl ether, 99%, stab. Each
36,38

Precio exclusivo en nuestra web

42,80
Ahorro 6,42 (15%)
A15691.0F Ethyl vinyl ether, 99%, stab. Each
132,60

Precio exclusivo en nuestra web

156,00
Ahorro 23,40 (15%)
A15000.0I Ammonium chloride, 98+% Each
155,55

Precio exclusivo en nuestra web

183,00
Ahorro 27,45 (15%)
A11766.0B Allyl bromide, 99%, stab. with 300-1000ppm Propylene oxide Each
107,20

Precio exclusivo en nuestra web

134,00
Ahorro 26,80 (20%)
L06004.0F Triethyl orthoacetate, 97% Each
353,60

Precio exclusivo en nuestra web

416,00
Ahorro 62,40 (15%)

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