Sodium in liquid ammonia—a versatile tool in modifications of arylphosphine oxides

A simple and practical method for modifications of tertiary arylphosphine oxides based on their reaction with sodium in liquid ammonia is presented. Depending on the structure of the starting compounds, either dearomatisation of the phenyl substituent or cleavage of a P-aryl bond from phosphorus ato...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Tetrahedron 2011-11, Vol.67 (45), p.8671-8678
Hauptverfasser:	Stankevič, Marek, Włodarczyk, Adam, Jaklińska, Magdalena, Parcheta, Renata, Pietrusiewicz, K. Michał
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Arylphosphine oxides Birch reduction Bonding Chemistry Cleavage Cyclic phosphine oxides Dearomatisation Exact sciences and technology Liquid ammonia Liquids Organic chemistry Organometalloidal and organometallic compounds Oxides P derivatives Phosphorus–aryl bond cleavage Preparations and properties Sodium Tetrahedrons
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	A simple and practical method for modifications of tertiary arylphosphine oxides based on their reaction with sodium in liquid ammonia is presented. Depending on the structure of the starting compounds, either dearomatisation of the phenyl substituent or cleavage of a P-aryl bond from phosphorus atom can be selectively performed and the corresponding (1,4-cyclohexadien-3-yl)phosphine oxides or secondary phosphine oxides were obtained in good to excellent yields. [Display omitted]
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2011.09.045