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

doi:10.1021/jo00416a003

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

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

168 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 language	English
Pages (from-to)	4271-4273
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	43
Issue number	22
DOIs	https://doi.org/10.1021/jo00416a003
State	Published - 1978

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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.",

author = "Ytzhak Ittah and Yoel Sasson and Israel Shahak and Shalom Tsaroom and Jochanan Blum",

year = "1978",

doi = "10.1021/jo00416a003",

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T1 - A New Aziridine Synthesis from 2-Azido Alcohols and Tertiary Phosphines. Preparation of Phenanthrene 9,10-Imine

AU - Ittah, Ytzhak

AU - Sasson, Yoel

AU - Shahak, Israel

AU - Tsaroom, Shalom

AU - Blum, Jochanan

PY - 1978

Y1 - 1978

N2 - 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.

AB - 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.

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

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