Aromatic substitution. 63. Friedel-Crafts alkylation of aromatics with 1-chloronorbornane, 3-halonoradamantane, and fluorocubane via their reactive sp3-hybridized …

…, CS Lee, GKS Prakash, RM Moriarty…

Index: Olah, George A.; Lee, Chang Soo; Prakash, G. K. Surya; Moriarty, Robert M.; Chander Rao, M. Suresh Journal of the American Chemical Society, 1993 , vol. 115, # 23 p. 10728 - 10732

Full Text: HTML

Citation Number: 24

Abstract

Abstract: 1-Chloronorbornane, 3-chloronoradamantane, and 3-bromonoradamantane, and fluorocubane, in the presence of aluminum chloride or boron trifluoride, respectively, readily alkylate benzene and substituted benzenes at or below room temperature. As back-side S~ Z-type displacement at bridgehead positions is not possible, the reported new Friedel-Crafts alkylations must involve strongly polarized bridgehead halide-aluminum chloride (or ...