Synthesis of N-Activated Aziridines of Long-Chain Fatty Acid Esters

Abstract

An alternative one-step synthesis of N-activated aziridines of naturally occurring fatty acid esters from olive oil and sunflower oil has been achieved. N-Tosylaziridine derivatives were obtained in yields ranging from 8.5 to 97.5%. Methyl cis- and trans-8-(3-octyl-1-tosylaziridin-2-yl)octanoates were formed with transesterified olive oil as substrate, and methyl cis- and trans-(Z)-11-(3-pentyl-1-tosylaziridin-2-yl)undec-9-enoates were produced when transesterified sunflower oil was the substrate.

Key words

aziridination - copper(II) acetylacetonate - olive oil ­methyl esters - sunflower oil methyl esters

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