OXIDATIVE FORMYLATION AND CHLOROMETHYLATION IN VILSMEIER REACTIONS OF O-AND S-HETEROCYCLIC KETONES

DOI: 10.1016/S0040-4020(01)86387-0

Source and publish data:

Tetrahedron p. 1303 - 1310 (1991)

Update date:2022-08-04

Topics:

Authors:

Giles, Paul R.

Marson, Charles M.

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Article abstract of DOI:10.1016/S0040-4020(01)86387-0

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.

Full text of DOI:10.1016/S0040-4020(01)86387-0

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