Journal of Organic Chemistry p. 5145 - 5150 (1990)
Update date:2022-07-29
Topics:
Tanko, James M.
Mas, Rosemal H.
The relative reactivities of several 9-alkylanthracenes toward bromine atom have been determined.Whereas for alkylbenzenes it is observed that isopropyl > ethyl > methyl, an inverted reactivity order was observed in the 9-anthryl system: methyl (1.00) > cyclopropyl (0.33) > ethyl (0.063) >> isopropyl (< 0.001), per α-hydrogen at 80 deg C.Stereoelectronic factors, specifically the alignment of the α-C-H bond with the anthryl ?-system, are implicated as bearing primary responsibility for this unusual reactivity order.In a general context, the relative importance of stereoelectronic effects vs the stability of the incipient radical in hydrogen atom abstraction from alkyl aromatics is discussed.
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Doi:10.1002/ardp.19903230409
(1990)Doi:10.1039/c1cc10196j
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