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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
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Efficient transformation of azides to primary amines using the mild and easily accessible CeCl3.7H2O/NaI system

Giuseppe Bartoli1, Giustino Di Antonio, Riccardo Giovannini

  • 1Dipartimento di Chimica Organica A. Mangini, Università di Bologna, viale Risorgimento 4, I-40136 Bologna, Italy.

The Journal of Organic Chemistry
|February 13, 2008
PubMed

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Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
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