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Digitale Medien

γ-Functionalisation of the 1-Phosphanorbornadiene Structure (1999)

Robin, Frédéric ; Mercier, François ; Ricard, Louis ; [weitere]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 1091-1097

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Details

ISSN: 1434-193X

Schlagwort(e): Phosphanorbornadiene ; Allylic metalation ; Allylic bromination ; BIPNOR dioxide ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: -3-Methyl-substituted 1-phosphanorbornadiene oxides or sulfides such as 1a,b are either metalated by a strong base (n-BuLi or LDA) or brominated by NBS at the methyl substituent. The reaction of the resulting delocalised carbanions 2a,b takes place either at C-2 (H+, MeI) or at the methylene group (Me3SiCl, ClPPh2, I2). In the last case, γ-functional (5a,b or 6a,b) or bridged (7) phosphanorbornadienes are obtained. Similarly, the reaction of 3-bromomethyl-1-phosphanorbornadiene oxides such as 8 with nucleophiles [NaCH(CO2Me)2, PhO-, Me2NH, PhCH2NH2] yields the corresponding γ-functional phosphanorbornadienes 9-12. This chemistry has also been applied to the BIPNOR dioxide 13.

Zusätzliches Material: 2 Ill.

Materialart: Digitale Medien

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