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Issue 10, 1988
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N-halogeno compounds. Part 9. N-Fluoroquinuclidinium fluoride—a new electrophilic fluorinating agent

Abstract

N-Fluoroquinuclidinium fluoride, prepared in high yield by treatment of a cold, dilute solution of quinuclidine in trichlorofluoromethane with fluorine at low pressure in a specially designed, virtually all glass vacuum system, acts as a site-selective electrophilic fluorinating agent towards carbanionic substrates [PhCNa(CO2Et)2→ PhCF(CO2Et)2; Me2CLiNO2→ Me2CFNO2; RMgX → RF (R = Ph, X = Br; R = c-C6H11, X = Cl); [graphic omitted]H2→ [graphic omitted]HF; PhSiCl3/F(in situ)→ PhF].

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Article information


J. Chem. Soc., Perkin Trans. 1, 1988, 2805-2811
Article type
Paper

N-halogeno compounds. Part 9. N-Fluoroquinuclidinium fluoride—a new electrophilic fluorinating agent

R. E. Banks, R. A. Du Boisson, W. D. Morton and E. Tsiliopoulos, J. Chem. Soc., Perkin Trans. 1, 1988, 2805
DOI: 10.1039/P19880002805

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