Lambert, Joseph B. published the artcileInductive enhancement of aryl participation, Related Products of bromides-buliding-blocks, the publication is Journal of the American Chemical Society (1977), 99(9), 3059-67, database is CAplus.
Enhanced participation by an aryl group in solvolysis could be achieved by placing an electron-withdrawing substituent vicinal to the leaving group. Acetolysis of meso-1,4-diaryl-2,3-butanediyl ditosylates and of 1,4-diaryl-2-butyl tosylates, in which the aryl groups were substituted with p-OMe, p-Me, H, p-Cl, m-CF3 and p-NO2, was examined The 2nd tosylate group provided the inductive stimulus for increased aryl participation. Comparison of the monotosylate with the ditosylate showed that the proportion of aryl participation increased from 93-9% for p-OMe, from 66-99% for p-Me, from 35-94% for H, and from 0-68% for p-Cl. Thus an electron-withdrawing substituent vicinal to the leaving group made the aryl-participation pathway essentially exclusive for aryl groups with substituents with σ ≥0. Even for a substituent with a small neg. σ value, such as p-Cl, participation could be quite significant in the ditosylate series, while completely lacking in the monotosylate series.
Journal of the American Chemical Society published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Related Products of bromides-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary