Tetrahedron p. 1303 - 1310 (1991)
Update date:2022-08-04
Topics:
Giles, Paul R.
Marson, Charles M.
The action of DMF-POCl3 at 20 deg C on tetrahydro-4H-pyran-4-one, tetrahydro-4H-thiopyran-4-one, chroman-4-one, and thiochroman-4-one affords the corresponding β-chlorovinylaldehydes.However, with excess DMF-POCl3 at 100 deg C, chroman-4-one affords 3-(chloromethyl)chromone, and thiochromanone gives 3-formylthiochromone.Mechanistic rationalisations are provided.
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