Polonski, Tadeusz;Milewska, Maria J.;Gdaniec, Maria;Gilski, Miroslaw published 《Molecular geometry and circular dichroism spectra of bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydrides and imides》 in 1993. The article was appeared in 《Journal of Organic Chemistry》. They have made some progress in their research.Category: tetrahydrofurans The article mentions the following:
Several tricyclic anhydrides and imides derived from optically active bicyclo[2.2.1]heptane-2,3-dicarboxylic acids were synthesized, and their CD spectra are reported. On the basis of MNDO calculations it was estimated that despite rigidity of the norbornane system, the five-membered rings of succinic anhydride and imide moieties are slightly twisted. The chromophores are flexible and can be more or less skewed depending on solvent polarity. The chromophore nonplanarity significantly influences magnitude and sign of the first Cotton effect associated with the lowest energy n-π* electronic transition. The sign of the second n-π* Cotton effect is governed by vicinal effect of substituents. The crystal structures of three N-(S)-1-phenylethylimides were solved to estimate the configuration of C-2 of the imide moieties.(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.Category: tetrahydrofurans 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