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

GILES, PR; MARSON, CM; (1991) OXIDATIVE FORMYLATION AND CHLOROMETHYLATION IN VILSMEIER REACTIONS OF O-HETEROCYCLIC AND S-HETEROCYCLIC KETONES. TETRAHEDRON , 47 (7) 1303 - 1310.

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Abstract

The action of DMF-POCl3 at 20-degrees-C on tetrahydro-4H-pyran-4-one, and thiochroman-4-oen affords the corresponding beta-chllorovinylaldehydes. However, with excess DMF-POCI3 at 100-degrees-C, chroman-4-one affords 3-(chloromethyl)chromone, and thiochromanone gives 3-formylthiochromone. Mechanistics rationalisations are provided.

Type:Article
Title:OXIDATIVE FORMYLATION AND CHLOROMETHYLATION IN VILSMEIER REACTIONS OF O-HETEROCYCLIC AND S-HETEROCYCLIC KETONES
Keywords:2-CYCLOHEXEN-1-ONES, PRODUCTS, ROUTE
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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