Reaction of 2-(α-bromoacetyl)-phenoxathiin with substituted o-, m-, or p-formyl-aroxides

Abstract

Solid sodium-or potassium aroxides with formyl and alkoxy substituents were reacted with 2-(α-bromoacetyl)-phenoxathiin 3 in the presence of crown ethers (15C5 or 18C6, respectively). When the formyl and hydroxy groups were in meta-or para-positions the resulting fluorescent compounds were 2-(α-formylaryloxyacetyl)-phenoxathiins 4a-d; however, when these substituents were in the ortho position, the fluorescent products were benzo[b]furyl 2-phenoxathiinyl ketones 5e-h, or naphtho[3,2-b]furyl 2-phenoxathiinyl ketone 8. The chromatographic behavior of compounds 4a-d, 5e-h, and 8 was investigated by TLC and reverse-phase-TLC (RP-TLC) for the hydrophobicity properties.