Aromatic chlorination of ω-phenylalkylamines and ω-phenylalkylamides in carbon tetrachloride and α, α, α-trifluorotoluene

JL O'Connell, JS Simpson, PG Dumanski…

Index: O'Connell, Jenny L.; Simpson, Jamie S.; Dumanski, Paul G.; Simpson, Gregory W.; Easton, Christopher J. Organic and Biomolecular Chemistry, 2006 , vol. 4, # 14 p. 2716 - 2723

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Citation Number: 12

Abstract

The aromatic halogenation of simple alkylbenzenes with chlorine proceeds smoothly in acetic acid but is much less efficient in less polar solvents. By contrast chlorination of ω- phenylalkylamines, such as 3-phenylpropylamine, occurs readily in either acetic acid, carbon tetrachloride or α, α, α-trifluorotoluene, and in the latter solvents gives high proportions of ortho-chlorinated products. These effects are attributable to the involvement ...

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