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The conversion of an aziridine plus an iminium salt to a 1,2-diamine

โœ Scribed by Matthew T. Hancock; Allan R. Pinhas

Book ID
104254385
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
173 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The conversion of an aziridine to a 1,2-diamine using lithium iodide and an iminium salt is discussed. We have found that when the aziridine is substituted by only alkyl groups, it is the less substituted carbon nitrogen bond that is broken; whereas, when the aziridine is substituted by a phenyl group at either the nitrogen or the carbon, it is the more substituted carbon nitrogen bond that is broken. For a 2,3-disubstituted aziridine, the reaction sequence goes with net retention of stereochemistry.

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A convenient and inexpensive conversion
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โœ Matthew T. Hancock; Allan R. Pinhas ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 108 KB

The conversion of an aziridine to the corresponding oxazolidinone using only carbon dioxide and a catalytic amount of lithium iodide is discussed. In all cases, either no reaction occurred or a high yield of product was obtained. HMPA has been added to the reaction mixture, as needed, to drastically