Unusual condensation of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with ( R)-phenylglycinol

Unusual condensation of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with ( R)-phenylglycinol

The reaction of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with ( R)-phenylglycinol proceeds via the intermediate formation of ( R,4 E,6 Z)-5,7-bis(trifluoromethyl)-2,3-dihydro-3-phenyl-1,4-oxazepine, which further undergoes a base-catalysed 1,3-proton shift followed by [1,2] Wittig rearrangement givin...

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Veröffentlicht in:Mendeleev communications 2006, Vol.16 (3), p.165-167
Hauptverfasser: Soloshonok, Vadim A., Ohkura, Hironari, Yasumoto, Manabu
Format: Artikel
Sprache:eng
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Zusammenfassung:The reaction of 1,1,1,5,5,5-hexafluoropentane-2,4-dione with ( R)-phenylglycinol proceeds via the intermediate formation of ( R,4 E,6 Z)-5,7-bis(trifluoromethyl)-2,3-dihydro-3-phenyl-1,4-oxazepine, which further undergoes a base-catalysed 1,3-proton shift followed by [1,2] Wittig rearrangement giving rise to 2,4-bis(trifluoromethyl)-6-phenylpyridine.
ISSN:0959-9436
DOI:10.1070/MC2006v016n03ABEH002298