Moriconi, Emil J.;Crawford, Wheeler C. published 《Reaction of chlorosulfonyl isocyanate with bridge bi- and tricyclic olefins》 in 1968. The article was appeared in 《Journal of Organic Chemistry》. They have made some progress in their research.HPLC of Formula: 14166-28-0 The article mentions the following:
The addition of ClSO2NCO to norbornene, norbornadiene, 7-benzoyloxy-, and 7-tert-butoxynorbornadiene, endo-, and exo-dicyclopentadiene, and bicyclo [2.2.2]octene (I) led, in each case, to a single, unrearranged cycloadduct, the N-chlorosulfonyl-β-lactam. A nonconcerted cycloaddition mechanism is proposed. Attempts to form the bis adduct from norbornadiene were unsuccessful. Assignment of the exo configuration to the azetidinone ring in these N-chlorosulfonyl-β-lactams is based predominantly on N.M.R. evidence. Benzenethiol-pyridine reduction of the N-chlorosulfonyl cycloadducts led to the corresponding unsubstituted β-lactams. The ir spectrum of exo-2-p-toluenesulfonamido-3-carboxybicyclo[2.2.1]heptane ultimately prepared from the norbornene cycloadduct expectedly differed from that of the endo isomer prepared by a stereospecific Lossen rearrangement on N-phenylsulfonyloxynorbornane-endo-2,3-dicarboximide. Treatment of N-phenylsulfonyloxynorbornane-exo-2,3-dicarboximide under Lossen conditions failed to yield a rearrangement product, as did the Hofmann reaction on norbornane-exo-2,3-dicarboximide and exo-2-carbomethoxy-3-carboxamidonorbornane. A Lossen rearrangement, however, successfully converted N-sulfonyloxybicyclo[2.2.2]octane-2,3-dicarboximide into 2-amino-3-carboxybicyclo[2.2.2]octane-HCl, identical with the acid hydrolysis product of the β-lactam cyclo-adduct from I. 50 references. To complete the study, the researchers used (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.HPLC of Formula: 14166-28-0 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