Beckmann Fragmentation and Successive Carbon–Carbon Bond Formation Using Grignard Reagents via Phosphonium Salt Intermediates

The intermediates formed during the Beckmann fragmentation of α-alkoxy and α-alkoxy-α-alkyl oxime acetates have been successfully trapped as phosphonium salts, which were subsequently reacted with a variety of Grignard reagents to give the corresponding substituted products in good yields. Notably,...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2016/07/01, Vol.64(7), pp.718-722
Hauptverfasser:	Fujioka, Hiromichi, Matsumoto, Nao, Kuboki, Yuichi, Mitsukane, Hidenobu, Ohta, Reiya, Kimura, Takashi, Murai, Kenichi
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetates - chemistry Beckmann fragmentation Carbon - chemistry carbon–carbon bond formation Grignard reagent Molecular Structure Organometallic Compounds - chemistry Organophosphorus Compounds - chemical synthesis Organophosphorus Compounds - chemistry Oximes - chemistry phosphonium salt intermediate
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container_title	Chemical & pharmaceutical bulletin
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creator	Fujioka, Hiromichi Matsumoto, Nao Kuboki, Yuichi Mitsukane, Hidenobu Ohta, Reiya Kimura, Takashi Murai, Kenichi
description	The intermediates formed during the Beckmann fragmentation of α-alkoxy and α-alkoxy-α-alkyl oxime acetates have been successfully trapped as phosphonium salts, which were subsequently reacted with a variety of Grignard reagents to give the corresponding substituted products in good yields. Notably, this reaction proceeded smoothly even from α-alkoxy-α-alkyl oxime acetates.
doi_str_mv	10.1248/cpb.c16-00006
format	Article
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subjects	Acetates - chemistry Beckmann fragmentation Carbon - chemistry carbon–carbon bond formation Grignard reagent Molecular Structure Organometallic Compounds - chemistry Organophosphorus Compounds - chemical synthesis Organophosphorus Compounds - chemistry Oximes - chemistry phosphonium salt intermediate
title	Beckmann Fragmentation and Successive Carbon–Carbon Bond Formation Using Grignard Reagents via Phosphonium Salt Intermediates
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