Process for the manufacture of 1-substituted-4-fluoro-1,4-diazon

Details Process for the manufacture of 1-substituted-4-fluoro-1,4-diazon Process for the manufacture of 1-substituted-4-fluoro-1,4-diazon

1996-05-06

1997-05-20

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

544337, 540472, 540542, 540567, C07D24700, C07D24504, C07D24314, C07F 906

Patent

active

056313721

ABSTRACT:
A process for producing 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts having the formula ##STR1## wherein the Z substituent is OH, OR, OC(O)R, SO.sub.3, SO.sub.2 R, NO.sub.2, NO, or PO(OR).sub.2, wherein R is an aryl or C.sub.1 -C.sub.8 alkyl group; n is 0, 1 or 2; each of R.sub.1, R.sub.2, R.sub.3, P.sub.4 and R.sub.5 independently represent hydrogen, C.sub.1 to C.sub.8 alkyl, or aryl 1-substituted-1,4-diazoniabicyclo[2.2.2]octane or 1,4-diazoniabicyclo[2.2.2]octane mono-N-oxide is reacted to attach the Z group and then the result is reacted with molecular fluorine in the presence of a solvent that substantially does not react with fluorine and a fluoride scavenger that results in an X counter ion. These compounds are useful as fluorinating agents for the introduction of fluorine into organic compounds.

REFERENCES:
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patent: 5086178 (1992-02-01), Banks
patent: 5367071 (1994-11-01), Syvret
Banks et al., 1-Alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Salts: a Novel Family of Electrophilic Fluorinating Agents, J. Chem. Soc., Chem. Commun., Jan. 29, 1992, p. 595.
Farkas et al., "Some Derivatives of 1,4-Diazabicyclo(2.2.2)octane (Triethylenediamine)", J. Chem. Eng. Data, vol. 13, No. 2, Apr. 1968.
Lal, "Site-Selective Fluorination of Organic Compounds Using 1-Alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane Salts (Selectfluor Reagents)," J. Org. Chem. 1993, 58, 2791-2796.
Murtagh, V., "Electrophilic Fluorination: An Introduction," Performance Chemicals, Aug./Sep. 1991, p. 36.
Umemoto et al., "N-Fluoropyridinium Triflate and Its Analogs, The First Stable 1:1 Salts of Pyridine Nucleus and Halogen Atom" Tetrahedron Letters, vol. 27, No. 28 (1986), pp. 3271-3274.
Gilicinski et al., "On the relative power of electrophilic fluorinating reagents of the N-F class," J. Fluorine Chemistry, 59, (1992) 157-162.
Organic Chemistry, Third Edition, R.T. Morrison and R.N. Boyd, p. 751.

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