Ring-opening Reactions Of Donor-Acceptor (D-A) Cyclopropanes With Cyclic And Thiol Ketals

Glycol and glycol ethers are known of developmental toxicity,and thus functionalized glycol diethers or their thiol analogues may be of great importance for the research of developmental toxicity.These products are difficult to synthesize by regular procedures,thus,it is of great significance to obtain these kinds of compounds by a simple and efficient method.The nucleophilic ring-opening reactions of donor-acceptor cyclopropanes with1,3-cyclohexanedione-derived cyclic ketals or 1,3-cyclohexanedione-derived cyclic thiol ketals were explored.These unsymmetric glycol diether compounds or unsymmetric dithiol diether compounds were obtained by the catalysis of Lewis acid copper trifluoromethanesulfonate.We screened and optimized the reaction conditions such as catalysts,solvents and temperature and determined the optimal conditions in this thesis.Moreover,a series of substrates were also expanded.The extended substrates exhibited well tolerance in these reactions.The stability of the products was also investigated and the experimental results shown that the glycol diethers or dithiol diethers would not easy to decompose within three days.Functionalized alkylene glycol diethers and dithiol diethers were obtained in good to high yields under mild conditions.A wide variety of functionalized substrates were applied in the reactions to give the corresponding products.