Neighboring group participation in solvolysis. VII. Trifluoroacetolysis of .OMEGA.-phenylakyl 6-methyl-2-naphthalenesulfonates.

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概要

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• The tide compounds, Ph(CH<SUB>2</SUB>)<I><SUB>n</SUB></I>OMns (<I>n</I>=2–6), were solvolyzed in buffered trifluoroacetic acid in order to elucidate the effect of a phenyl group at a remote position on the reactivity and the course of the reaction. The reactivities varied remarkably with the length of the alkyl chain(<I>n</I>); 2>>3<<4>5>6. The rate enhancement was attributed to anchimeric assistance by a remote phenyl group, and the rate depression to the electron-withdrawing inductive effect of a phenyl group. Studies on reaction products revealed that in trifluoroacetolysis of 4-phenylbutyl menasylate (<I>n</I>=4) the only pathway to take place is the one with δ-phenyl participation, and that even for 5-phenylpentyl menasylate (<I>n</I>=5) 12% of the reaction proceeds <I>via</I> ε-phenyl participation.

• 公益社団法人 日本化学会の論文

著者

• Saito Yoshimasa

  The Institute of Scientific and Industrial Research, Osaka University

関連論文

• Neighboring group participation in solvolysis. VII. Trifluoroacetolysis of .OMEGA.-phenylakyl 6-methyl-2-naphthalenesulfonates.
• Neighboring group participation in solvolysis. X. Dissection of Ar1-5 and Ar2-6 pathways in trifluoroacetolysis of 4-arylbutyl 6-methyl-2-naphthalenesulfonates.

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