Cycloaddition of tungsten−η1-3-furyl compounds with a variety of organic alkenes and
alkynes proceeds smmothly at ambient conditions, yielding tungsten−η1-oxabicyclo[2.2.1]heptene and −η1-oxabicyclo[2.2.1]heptadiene compounds in high regioselectivities and
stereoselectivities. The cycloaddition is proposed to proceed via a mechanism involving a
zwitterion intermediate. Cleavage of oxygen bridges of η1-oxabicyclo[2.2.1]heptenes and η1-oxabicyclo[2.2.1]heptadienes occurs on treatment of CF3SO3H and Lewis acid, leading to
atypical carbon−carbon bond scission and deoxygenation reactions to give highly substituted
benzene and furan derivatives, respectively. The role of the tunsten fragment in these
demetalation reactions is discussed in detail.
Treatment of tungsten-q~-7-oxabicyclo[2.2. llheptadiene and -q1-7-oxabicyclo[2.2.l]heptene with CF3S03H leads to atypical carbon-carbon bond scission and deoxygenation; the reaction intermediates in the bond scission involves a tungstenq 1-2-h ydrofurylium cation.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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.