A New Aziridine Synthesis from 2-Azido Alcohols and Tertiary Phosphines. Preparation of Phenanthrene 9,10-Imine

Ytzhak Ittah, Yoel Sasson, Israel Shahak, Shalom Tsaroom, Jochanan Blum

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163 Scopus citations

Abstract

A new stereospecific synthesis of aziridines is described. It consists of the reaction of sodium azide with an oxi-rane, followed by treatment of the 2-azido alcohol formed with a tertiary phosphine. The method has been applied for the preparation of the first unsubstituted phenanthrene imine. The synthesis of 1a,9b-dihydrophenanthr[9.10-6]azirine proved to proceed via a phosphonium hydroxide intermediate which could be isolated under mild conditions. The unsubstituted arene imine proved to be thermally stable (up to 190 °C), but rearranges to 9-aminophe-nanthrene in the presence of hydrochloric acid.

Original languageEnglish
Pages (from-to)4271-4273
Number of pages3
JournalJournal of Organic Chemistry
Volume43
Issue number22
DOIs
StatePublished - 1978

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