2011OrganometallicsRequires access

Homoannular Double Friedel–Crafts Acylation of Phosphametallocenes

Masamichi Ogasawara, Morihiko Ogura, Takeshi Sakamoto, Susumu Watanabe, Sachie Arae, Kiyohiko Nakajima, Tamotsu Takahashi

Open publisher page 8 citations

Abstract

Two reaction modes of homoannular double Friedel–Crafts acylation are realized using polyalkylphosphametallocenes as substrates. The first example is the reaction of tetra( tert -butyl)diphospharuthenocene with excess acetyl chloride/aluminum chloride, giving a 2,3-double Friedel–Crafts acylation product with an elimination of one of the tert -butyl groups. The other is the 2,5-diacylation of 1′,2′,3,3′,4,4′,5′-Me 7 -phosphaferrocene using an acyl chloride/aluminum chloride mixture. These reactions provide rare examples of doubly functionalized phosphametallocenes.

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What this paper is about

Two reaction modes of homoannular double Friedel–Crafts acylation are realized using polyalkylphosphametallocenes as substrates. The first example is the reaction of tetra( tert -butyl)diphospharuthenocene with excess acetyl chloride/aluminum chloride, giving a 2,3-double Friedel–Crafts acylation product with an elimination of one of the tert -butyl groups. The other is the 2,5-diacylation of 1′,2′,3,3′,4,4′,5′-Me 7 -phosphaferrocene using an acyl chloride/aluminum chloride mixture. These reactions provide rare examples of doubly functionalized phosphametallocenes.

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Available abstract

Two reaction modes of homoannular double Friedel–Crafts acylation are realized using polyalkylphosphametallocenes as substrates. The first example is the reaction of tetra( tert -butyl)diphospharuthenocene with excess acetyl chloride/aluminum chloride, giving a 2,3-double Friedel–Crafts acylation product with an elimination of one of the tert -butyl groups. The other is the 2,5-diacylation of 1′,2′,3,3′,4,4′,5′-Me 7 -phosphaferrocene using an acyl chloride/aluminum chloride mixture. These reactions provide rare examples of doubly functionalized phosphametallocenes.

Key concepts: Friedel–Crafts reaction, Acylation, Chemistry, Chloride, Acetyl chloride, Benzoyl chloride, Acyl chloride, Aluminium

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Homoannular Double Friedel–Crafts Acylation of Phosphametallocenes — Research Paper | ScholarLens