Metal carbonyl salts CpW(CO) 3 Na, Re(CO) 5 Na, and CpFe(CO) 2 Na were used for intramolecular cyclization of 1-(3-bromo-1-propynyl)-2-(3-oxopropyl)benzene. Among these salts, CpW(CO) 3 Na was found to be the most effective in yielding a metalated fused η 1 -2,5-dihydro-3-furyl complex. To generalize this cyclization, a number of organic substrates containing propargyl bromide and tethered aldehyde or ketone were prepared. Cyclizations of these substrates by CpW(CO) 3 Na proceeded with moderate yields (50%-65%), producing fused tungsten-η 1 -2,5-dihydrofur-3-yl compounds of five-, six-, and seven-membered rings. Demetalations of these organometallic products by (NH 4 ) 2 Ce(NO 3 ) 6 in CH 3 OH/CH 2 Cl 2 under flowing CO provided fused 3-(methoxycarbonyl)-2,5dihydrofurans; the yields were 50-60% for most cases. Consecutive oxidations of the representative η 1 -2,5-dihydrofur-3-yl complex 15 to its fused η 1 -2-furyl and further to η 1 -butenolide derivative were accomplished in good yields. Demetalations of these two fused η 1 -heterocycles were successful for η 1 -butenolide but not for the η 1 -2-furyl derivative.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.