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The Synthesis of RGD-functionalized Hydrogels as a Tool for Therapeutic Applications
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2-Hydroxy-5-nitrobenzyl as a diazeniumdiolate protecting group: application in NO-releasing polymers with enhanced

Hua Xu1, Melissa M Reynolds, Keith E Cook

  • 1Department of Chemistry, Johns Hopkins University, Baltimore, Maryland 21218, USA.

Organic Letters
|September 25, 2008
PubMed

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This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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