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20-September-2008 09:55:59 - Benzyl The structure of a benzyl cation The structure of a benzyl cation In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-. The abbreviation Bn is frequently used to denote benzyl moieties in nomenclature and structural depictions of chemical compounds. For example, benzyl alcohol can be represented as BnOH. This abbreviation is not to be confused with Bz, which is the abbreviation for the benzoyl group C6H5CO-. The term benzyl is also used in reference to the carbocation1, anion, and free radical2 moieties featuring a benzene ring attached to a CH2 group, in which the CH2 group bears a positive charge, a negative charge, or a single unpaired electron respectively. 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: reaction of alcohol with benzyl bromide and a strong base such as sodium hydride as in a Williamson ether synthesis3 reaction of alcohol with an imidate such as benzyl trichloroacetimidate C6H5CH2OCCCl3=NH promoted by trifluoromethanesulfonic acid. An example forming a p-methoxybenzyl PMB ether in total synthesis 4: Benzyl ether protective group White 1998 The benzyl group can be removed by hydrogenation. PMB ethers can be cleaved by magnesium bromide -dimethyl sulfide, CAN or DDQ 5. One study 6 employs a benzyl pyridinium salt as a benzyl donor for alcohols: Pyridinium salt benzyl ether protection 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 ^ Carey, F. A., and Sundberg, R. J.; Advanced Organic Chemistry, Part A: Structure and Mechanisms, 5th ed.; Springer: New York, NY, 2008. pp 806-808. ^ Carey, F. A., and Sundberg, R. J.; Advanced Organic Chemistry, Part A: Structure and Mechanisms, 5th ed.; Springer: New York, NY, 2008. pp 312-313. ^ DeSelms, R. H.; Benzyl Phenyl Ether Compounds; Enigen Science Publishing: Washington, DC, 2008. ^ 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 ^ Protecting groups Krzysztof Jarowicki and Philip Kocienski J. Chem. Soc., Perkin Trans. 1, 1998, 4005-4037 4005 doi:10.1039/a803688h ^ 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. Retrieved from http://en..org/wiki/Benzyl Categories: Functional groups | Protecting groups Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français 日本語 Português Svenska 中文 This page was last modified on 4 July 2008, at 19:2
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