ChemInform Abstract: Preparation and Ring-Opening Reactions of N-Diphenylphosphinyl Vinyl Aziridines.

✍ Scribed by A. A. CANTRILL; A. N. JARVIS; H. M. I. OSBORN; A. OUADI; J. B. SWEENEY

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199708111

✦ Synopsis

Preparation and Ring-Opening Reactions of N-Diphenylphosphinyl Vinyl Aziridines. -LDA-Lithiation of allyl bromide (I) followed by ZnCl2 generates α -bromo allyllithium which reacts with phosphinyl aldimines to form mainly trans-or cis-aziridines depending on the substituent R. The arylated trans-derivatives (cf. (IIIa)) react with a variety of carbon nucleophiles to yield selectively or exclusively the C-3 attack products. Chalcogen nucleophiles such as (XI) give mainly the C-2 ring opened product (cf. (XIII)). -(CANTRILL, A. A.