Csende, Ferenc;Stajer, Geza published 《A convenient reduction of unsaturated bicyclic anhydrides》. The research results were published in《Organic Preparations and Procedures International》 in 1999.COA of Formula: C9H10O3 The article conveys some information:
Bicyclic anhydrides such as I are hydrogenated in 89-98% yields to saturated bicyclic anhydrides such as II by using cyclohexene as a transfer hydrogenation substrate in the presence of palladium on carbon. E.g., I dissolved in THF is treated with 2 equivalent of cyclohexene in the presence of palladium on carbon and refluxed for 8-12 h to give II in 98% yield. The modified procedure avoids the use of flammable reagents such as Raney nickel or mol. hydrogen. The experimental procedure involved many compounds, such as (3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione (cas: 14166-28-0) .
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.COA of Formula: C9H10O3 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