Mechanisms of circumambulatory rearrangements of 5-halogeno-1,2,3,4,5-pentamethoxycarbonylcyclopentadienes View Full Text


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Article Info

DATE

2015-09

AUTHORS

G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin

ABSTRACT

Possible paths of halogen atom migration in 5-halogeno-1,2,3,4,5-pentamethoxycarbonylcyclopentadienes were studied using the density functional theory. The calculations revealed preferential 1,5(in comparison with 1,3-) sigmatropic shifts of halogen atoms along the perimeter of the five-membered ring with the energy barriers ΔEZPE≠ = 42.9, 26.9, 19.8, and 15.4 kcal mol–1 for the fluoro-, chloro-, bromo-, and iodosubstituted derivatives, respectively. The calculated charges of halogen atoms in the structures of transition states for 1,5-shifts change from negative for the fluorine atom to positive for the iodine atom (–0.356 (F), 0.019 (Cl), 0.052 (Br), 0.184 e (I)). The migration capacity increases in the order F < Cl < Br < I with an increase in the atomic radius of halogen. More... »

PAGES

2043-2049

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-015-1115-z

DOI

http://dx.doi.org/10.1007/s11172-015-1115-z

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1034697722


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