Novel sequence of two base-catalyzed 1,3 proton shifts and [1,2] Wittig rearrangement in the synthesis of 2,4-bis-(trifluoromethyl)-6-phenylpyridine

The reaction of 1,1,1,5,5,5-hexafluoro-2,4-pentanedione with (R)-phenylglycinol was found to proceed via intermediate formation of (R, 4E, 6Z)-5,7-bis-(trifluoromethyl)-2,3-dihydro-3-phenyl-1,4-oxazepine which further underwent a base-catalyzed 1,3-proton shift reaction followed by [1,2] Wittig rearrangement giving rise to 2,4-bis-(trifluoromethyl)-6-phenylpyridine.

Figure optionsDownload as PowerPoint slide