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Benzyl chloride also reacts readily with metallic magnesium to produce a Grignard reagent. [5] It is preferable over benzyl bromide for the preparation of this reagent, since the reaction of the bromide with magnesium tends to form the Wurtz coupling product 1,2-diphenylethane .
Benzyl group and derivatives: Benzyl group, benzyl radical, benzyl amine, benzyl bromide, benzyl chloroformate, and benzyl methyl ether. R = heteroatom, alkyl, aryl, allyl etc. or other substituents. In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure R−CH 2 −C 6 H 5.
A simple example is methyl chloroformate, which is commercially available. Chloroformates are used as reagents in organic chemistry. For example, benzyl chloroformate is used to introduce the Cbz (carboxybenzyl) protecting group and fluorenylmethyloxycarbonyl chloride is used to introduce the FMOC protecting group. Chloroformates are popular in ...
Benzyl chloroformate, also known as benzyl chlorocarbonate or Z-chloride, is the benzyl ester of chloroformic acid. It can be also described as the chloride of the benzyloxycarbonyl (Cbz or Z) group. In its pure form it is a water-sensitive oily colorless liquid, although impure samples usually appear yellow.
An example of a Schotten-Baumann reaction. Benzylamine reacts with acetyl chloride under Schotten-Baumann conditions to form N-benzylacetamide. Schotten–Baumann reaction also refers to the conversion of acid chloride to esters. The reaction was first described in 1883 by German chemists Carl Schotten and Eugen Baumann. [1] [2]
Also, there are no carbocation rearrangements, as the acylium ion is stabilized by a resonance structure in which the positive charge is on the oxygen. The viability of the Friedel–Crafts acylation depends on the stability of the acyl chloride reagent. Formyl chloride, for example, is too unstable to be isolated.
Orthogonal protection is a strategy allowing the specific deprotection of one protective group in a multiply-protected structure. For example, the amino acid tyrosine could be protected as a benzyl ester on the carboxyl group, a fluorenylmethylenoxy carbamate on the amine group, and a tert-butyl ether on the phenol
Ethyl cyanoacetate is a building block for the synthesis of heterocycles which are used for example as drugs: Allopurinol , used for the treatment of chronic gout, can be synthesized starting with a Knoevenagel condensation with triethyl orthoformate ; the condensation product is cyclized with hydrazine to give a substituted pyrazole and ...