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 language | English |
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Pages (from-to) | 4271-4273 |
Number of pages | 3 |
Journal | Journal of Organic Chemistry |
Volume | 43 |
Issue number | 22 |
DOIs | |
State | Published - 1978 |