My watch list
my.chemeurope.com  
Login  

Benzyl



  In organic chemistry, benzyl is the term for the anion C6H5CH2-, which can be obtained formally by deprotonation of toluene. The benzyl functional group is sometimes abbreviated "Bn", not to be confused with "Bz", which is short for the benzoyl group. For example, benzyl alcohol can be abbreviated to BnOH.

Additional recommended knowledge

In substituent nomenclature, benzyl and phenyl are commonly confused. Benzyl can be seen as a phenyl attached to a CH2 before attaching to the parent compound.

Benzyl protective groups

Benzyl groups are frequently used in organic synthesis as protective group for alcohols and carboxylic acids.

Two common methods for benzyl ether protection:


The benzyl group can be removed by hydrogenation. PMB ethers can be cleaved by magnesium bromide –dimethyl sulfide, CAN or DDQ [2].

One study [3] employs a benzyl pyridinium salt as a benzyl donor for alcohols:

The solvent is trifluoromethylbenzene and magnesium oxide is an acid scavenger. The reaction type for this conversion is believed to be SN1 based on the detection of trace amounts of Friedel-Crafts reaction sideproducts with toluene as a solvent.

References

  1. ^ Total synthesis of rutamycin B via Suzuki macrocyclization James D. White, Thomas Tiller, Yoshihiro Ohba, Warren J. Porter, Randy W. Jackson, Shan Wang, and Roger Hanselmann 80 Chem. Commun., 1998 doi:10.1039/a707251a
  2. ^ Protecting groups Krzysztof Jarowicki and Philip Kocienski J. Chem. Soc., Perkin Trans. 1, 1998, 4005–4037 4005 doi:10.1039/a803688h
  3. ^ K. W. C. Poon and G. B. Dudley (2006). "Mix-and-Heat Benzylation of Alcohols Using a Bench-Stable Pyridinium Salt". J. Org. Chem. 71 (10): 3923-3927. doi:10.1021/jo0602773.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Benzyl". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE