Canonne, Persephone;Belanger, Denis;Lemay, Gilles published 《Novel synthesis of five- and six-membered spiro γ-lactones in rigid bicyclic systems》. The research results were published in《Journal of Organic Chemistry》 in 1982.Name: (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione The article conveys some information:
The reaction of bis(bromomagnesio)alkanes with bridged tricyclic endo– and exo-dicarboxylic anhydrides and their dihydro derivatives provides a general and versatile route to corresponding tricyclic spiro γ-butanolides. Further extension of this methodol. to the dianhydride of bicyclo[2.2.2]octene showed appreciable regioselectivity. The subsequent transformation of spiro γ-lactones into 4-spiro-2-butenolides by retro-Diels-Alder reaction has provided a simple and convenient synthesis of these mols. Proton and 13C NMR spectra are reported for most of the compounds(3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) were involved in the experimental procedure.
In the laboratory, (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione(14166-28-0) is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes.Name: (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.
Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem