Photochemical Bromination of Methyl (E)-2-Methylbut-2-enoate with N-Bromosuccinimide: Formation of 4-Bromo-2-methylbut-2-en-4-olide
Bromination of methyl (E)-2-methylbut-2-enoate (4) with N-bromosuccinimide under irradiation with light was described.The formation of 4-bromo-2-methylbut-2-en-4-olide (8) in fairly good yield together with the desired methyl (E)-4-bromo-2-methylbut-2-enoate (5), methyl (E)-2-(bromomethyl)but-2-enoate (6), and methyl 2,3-dibromo-2-methylbutanoate (7) was clarified.Methyl (E)-4-(p-formylphenoxy)-2-methylbut-2-enoate (16) was smoothly subject to catalytic hydrogenation using Wilkinson complex, while the rate of the hydrogenation of its geometrical isomer (17) was extremely retarded.
Ishii, Hisashi,Ishige, Marie,Matsushima, Yoko,Tohojoh, Toshiaki,Ishikawa, Tsutomu,Kawanabe, Eri
p. 2353 - 2360
(2007/10/02)
Studies on the Chemical Constituents of Rutaceous Plants. Part 45. Novel Phenyl Propanoids: Cuspidiol, Boninenal, and Methyl Boninenalate
Cuspidiol, boninenal, and methyl boninenalate were established as having the structures 3-phenyl>propanol (1), (E)-3-phenyl>propenal (2), and (E)-3-phenyl>propenal (3) respectively.The three compounds were also independently synthesized.