Benzyl group

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Benzyl group ( blue ) above, from left to right, as part of a molecule, as a benzyl radical and in benzylamine and below, from left to right, in benzyl bromide, benzyl chloroformate and benzyl methyl ether. R = hetero atom, organyl radical, such as alkyl , aryl , allyl, etc. or other radicals with a free valence.

In organic chemistry, the benzyl group , older α-tolyl group , is the phenylmethylene group –CH 2 -C 6 H 5 ; The following abbreviations, some of which are ambiguous and are not regulated by any IUPAC guideline, are used for benzyl : Bn (also stands for the benzylidene group ), Bz (also stands for the benzoyl group), more rarely the unequivocal abbreviations Bzl or CH 2 Ph . Examples of compounds having a benzyl group areBenzyl alcohol , benzylamine , benzyl chloride and the benzyl butyl phthalate (BBP) used as a plasticizer .

The benzyl group is used in peptide chemistry, carbohydrate chemistry and in many total syntheses of natural products as a protective group for heteroatoms because it can easily be split off again hydrogenolytically , ie under mild conditions. The only by-product is volatile toluene .

The benzylation , ie introduction of a benzyl group in a compound is usually by a substitution reaction with benzyl halides.

literature

  • Philip J. Kocieński: Protecting Groups. Thieme, Stuttgart / New York 1994, ISBN 3-13-135601-4 .

See also