Chi, Ki Whan published the artcileA substituent effect on the palladium(II) catalyzed [3,3]-sigmatropic rearrangement of allylic esters, Safety of 3-Methylbut-2-en-1-yl benzoate, the publication is Bulletin of the Korean Chemical Society (1994), 15(2), 98-100, database is CAplus.
To a solution of I( X=p-MeO,p-Me,p-Cl,m-CF3,p-NO2, etc.) in THF at 25° was added bis(acetonitrile)palladium(II) chloride catalysts to yield II(X as above) in more than 97% GC yield. Pseudo-first-order rate constants(kp) were obtained by least-square method from the slope of substrate concentration vs. time; the second-order rate constants(k2) were then calculated from a division of kp by the concentration of catalysts. A Hammett plot of k2 vs. σ shows a good linear correlation (s=0.977) and retardation of the reaction rate is directly proportional to the strength of electron-withdrawing ability of the substituents (ρ= -1.05). A cyclization-induced mechanism was postulated. Since the rate decreases proportional to σ, the rate-determining step is the second step in which the pos.-charged intermediate is produced,. The small absolute value of ρ is attributed to the delocalization of pos. charge over the neighboring oxygen atoms in the transition state.
Bulletin of the Korean Chemical Society published new progress about 5205-11-8. 5205-11-8 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Benzene,Ester, name is 3-Methylbut-2-en-1-yl benzoate, and the molecular formula is C12H14O2, Safety of 3-Methylbut-2-en-1-yl benzoate.
Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics