One pot synthesis of polycyclic oxygen aromatics. Part IV reaction of THP ether of 2-bromomethyl phenols

✍ Scribed by Tirumalai R. Kasturi; Asish B. Mandal; Bangalore G. Sumana; Betagiri Rajasekhar

• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 754 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)86351-1

✦ Synopsis

Reaction of 2-bromomethyl-I-(2'-tetrahydropyranyloxy) benzene 3a with tetrachlorocatechol(TCC) in acetone in presence of anhydrous K&O3 resulted in the formation of diastereomeric products to benzofuranl which cis & tram+ 6-chlor~~hydroxy-&(2-oxopropyl)spiro[9&benzo[a]xanthen-9,2'(I'H) -7(8H)-one eaj. Similk reaction o ! 7a & 8a) structures were assigned, along with tetrachlorocatechol ethers (Sa & 3a with tetrabromocatechol(TBC) g ave the expected monobromo compounds 7d & 8d along with the ethers 5d & 6d. When the reaction was repeated with substrates 3b-c with TCC/TBC in ketonic solvents(acetone/methyl ethyl ketone), the corresponding compounds Sb-c to 8b-c, 5e-f to G-f, 7e-g & &e-h were obtained. A suitable explanation has been given for the formation of acetonyl compound 6 in this reaction.