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Conversion of aziridine-2-carboxylic esters into 2H-azirine-2-carboxylic esters

✍ Scribed by Johan Legters; Lambertus Thijs; Binne Zwanenburg

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 371 KB
Volume: 111
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19921110203

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✦ Synopsis

Abstract

Aziridine‐2‐carboxylic esters 1 were converted into 2__H__‐azirine‐2‐carboxylic esters 4 in two steps. Treatment of 1 with tert‐butyl hypochlorite in ether gave smooth N‐chlorination. Reaction of N‐chloroaziridines 2 with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) or 1,4‐diazabicyclo[2.2.2]‐octane (DABCO) gave 2H‐azirine‐2‐carboxylic esters 4 in moderate yields, with concomitant formation of aziridines 1. Aziridines 1 could readily be N‐brominated with N‐bromosuccinimide. Treatment of N‐bromoaziridines 3 with base, however, did not lead to azirine formation. N‐Halogenated aziridines 2 and 3 exist as mixtures of invertomers, which slowly interconvert in solution.

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