High pressure-assisted synthesis of 1,2,3-trialkyldiaziridines from N-chloroalkylamines

✍ Scribed by Vladimir V. Kuznetsov; Julia S. Syroeshkina; Dmitrii I. Moskvin; Marina I. Struchkova; Nina N. Makhova; Alexey A. Zharov

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2008
• Tongue: English
• Weight: 453 KB
• Volume: 45
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570450230

✦ Synopsis

Abstract

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New method for the preparation of 1,2,3‐trialkyldiaziridines 1 in high yields, based on the transformation of N‐chloroalkylamines 3 without using carbonyl compounds in the presence of primary aliphatic amines with the same alkyl fragment, potassium carbonate and a small amount of water in CHCl~3~ under high pressure (500 MPa), was developed. Diaziridines 1 can be synthesized in the same conditions using a larger amount of potassium carbonate instead of primary aliphatic amines however in lower yields. The kinetic investigations on the synthesis of 1,2‐diethyl‐3‐methyldiaziridine 1a from N‐chloroethylamine 3a have shown that the reaction leading to diaziridine 1a proceeds according to the law of the second order.