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
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Sprache:eng
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Zusammenfassung: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.c16-00006