82571-47-9Relevant academic research and scientific papers
Donor-Atom Effects on Relative E2 Rate Constants for Reactions of Anions with Cyclohexyl Bromide
Bordwell, Frederick G.,Mrozack, Susan Romberg
, p. 4813 - 4815 (1982)
2-Naphthoxide oxanions and carbazole nitroanions react with cyclohexyl bromide in Me2SO solution to give cyclohexene, whereas 9-methylfluorene carbanions give substitution and benzenethiolate thianions give both elimination and substitution.The relative order of E2 rate constants for anions of the same basicity is ArS(1-) > 2-NpO(1-) > Cb(1-) > 9-MeFl(1-).
Photochemical generation of 9h-fluorenyl radicals
Dyblenko, Tatiana,Chtchemelinine, Andrei,Reiter, Ryan,Chowdhury, Ruhul Q.,Enaya, Alexander,Afifi, Hanan,Fournier, Rene,Mladenova, Gabriela,Lever, Alfred Barry P.,Lee-Ruff, Edward
, p. 470 - 475 (2014/04/03)
A series of 9-substituted fluorenols and 9,9′-disubstituted-9, 9′-bifluorenyls were irradiated to give products derived from fluorenyl radicals. Product distribution was solvent dependent. A TEMPO adduct was isolated from the photoexcitation of 9-fluorenol. An unusual unsymmetrical 3,9′-bifluorenyl was observed from the photolysis of 9- trifluoromethylfluorenol and 9,9′-di(trifluoromethyl)-9,9′- bifluorenyl in more polar or hydrogen-bonding solvents. The electronic nature of 9-substituted fluorenyl radicals was probed using theoretical calculations showing the dipolar character of species with electron-deficient groups. These constitute the first examples of "doubly destabilized" radicals. Substituted 9-fluorenols and 9,9′-bifluorenyls undergo photolysis to give products derived from 9-fluorenyl radicals. These intermediates decay by hydrogen abstraction giving 9H-fluorenes, or coupling to 9,9′bifluorenyls. The 9-trifluoromethyl-9-fluorenyl radical undergoes an unusual coupling to the unsymmetrical 9,3′-bifluorenyl.
SN2 Reactions of Carbanions with Primary and Secondary Alkyl Bromides in Dimethyl Sulfoxide Solution
Bordwell, Frederick G.,Mrozack, Susan Romberg
, p. 3802 - 3803 (2007/10/02)
9-Methylfluorenyl carbanions undergo SN2 reactions with cyclohexyl, isopropyl, isobutyl and n-butyl bromides in high yields in Me2SO solution with the relative rates of (1.0), 6.4, 8.6 and 56 respectively.
