2,4-Bis(fluorocarbon)-substituted phenols for high yield Newman–Kwart rearrangement reactions

The Newman–Kwart thermal rearrangement of two 2,4-disubstituted O-arylthiocarbamates, prepared from the corresponding phenols, is reported. Clean conversion to the S-arylthiocarbamates in high yields was observed. The rearrangement appears to be facilitated by the presence of electron-withdrawing substituents in the 2- and 4-positions of the aromatic ring.

The O-thiocarbamates of 2,4-disubstituted phenols with fluorinated groups undergo facile and high yielding Newman–Kwart thermal rearrangement reactions to the corresponding S-thiocarbamates, allowing the preparation of thiophenols with bulky groups in the 2-position of the aromatic ring.Figure optionsDownload as PowerPoint slide