87384-00-7Relevant academic research and scientific papers
Photochemical addition of cyclic ethers/acetals to olefins using tBuOOtBu: Synthesis of masked ketones/aldehydes and diols
Hayakawa, Mamiko,Shimizu, Rina,Omori, Hajime,Shirota, Hisashi,Uchida, Kou,Mashimo, Hiroshi,Xu, Han,Yamada, Ryuusei,Niino, Seiya,Wakame, Yoshiki,Liu, Chuanxiang,Aoyama, Tadashi,Ouchi, Akihiko
, (2020/09/18)
A fast photochemical C–C bond formation between cyclic ethers/acetals and olefins using di-tert-butyl peroxide (DTBP) was developed. This method provides easy access to 2-substituted cyclic ethers, and 2- or 4-substituted cyclic acetals. Acyl/formyl groups or diols can be obtained by the hydrolysis of the 2- or 4-substituted cyclic acetals, respectively. The reactions proceeded at room temperature and gave the expected products in good to excellent yields; efficient reactions were completed within 0.5 h at room temperature in >95% yield.
CYCLOPROPANATION OF DIMETHYL FUMARATE AND MALEATE WITH GEM-DIHALIDES CATALYZED BY Co(0)- OR Ni(0)-COMPLEX AND ZINC.
Kanai,Nishiguchi,Matsuda
, p. 1592 - 1597 (2007/10/02)
The reaction of bis(acetonitrile)bis(diethyl fumarate)cobalt(0) with dibromomethane gave diethyl trans-1,2-cyclopropanedicarboxylate in a 67% yield based on the cobalt complex. Dimethyl cis-1,2-cyclopropanedicarboxylate was obtained in a 52% yield from the reaction of dimethyl maleate with dibromomethane in the presence of acetonitrilebis(dimethyl maleate)nickel(0) accompanied by the formation of the trans-isomer in a 14% yield. The addition of zinc gave cyclopropanes in over 100% yields based on cobalt or nickel. 3-Methyl- and 3,3-dimethyl-1,2-cyclopropanedicarboxylic acid esters were produced by the reaction of dimethyl fumarate or maleate with 1,1-dibromoethane and 2,2-dibromopropane. The yield in the cobalt catalyst system decreases with an increase of substituents of gem-dibromides, while that in the nickel catalyst system does not vary appreciably.
