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STATEMENT OF THE PROBLEM 4
STABILITY AND CHEMICAL REACTIVITY IN BORAZAROFUROPYRIDINES
2,3-dibromofuran 3-bromofuran 3-furancarboxaldehyde 4(furan 4(thiophene additional stirring aldehyde allowed to warm analytical sample anhydrous benzene anhydrous ether cooled aqueous phase aromatic character benzene borazarofuropyridines boronic acid bromination Calcd carbon chloride cis and trans cis isomer cm"l compounds cooled to 70 corresponding dried over magnesium dried over MgSO electrophilic substitution ethanol ether was added etheral ethyllithium ethyllithium was added evaporated fractionated furan furfural furothienotropylium ions G.l.c. analysis hexane hydrazine hydrogen-deuterium exchange hydrogenation hydrolysis IR(film isomer distribution isomeric ketone layers were separated Literature value lithiumaluminum hydride M.wt mass spectra minutes mixture was stirred ml of anhydrous mmole mole N,N-dimethylformamide NMR CDCl obtained olefin phase was extracted phases were washed phosphonate phosphoranes ppm complex ppm triplet preparation reaction mixture reactive recrystallized refluxed room temperature sample was recrystallized Scheme sodium methoxide stirred solution thiophene trans isomer tropylium ion l8 Wittig reaction XIX and XX yield