Gaseous N2O4 reacts with 18-crown-6 to afford a stable ionic complex of NO+·18-crown-6·H(NO3)2-; this complex is an efficient nitrosating agent for the conversion of thiols to their corresponding S-nitrosothiols in different organic solvents.
References
1.
(a) WilliamsD. L. H., The Chemistry of Amino, Nitroso, Nitro and Related Groups, Wiley, New York, 1996, pp. 665–682, and references cited therein; (b) L. K. Keefer and D. L. H. Williams, Methods in Nitric Oxide Research, Wiley, New York, 1966, pp. 509–519.
2.
OaeS., KimY. H., and FukushimaD., Chem. Lett., 1977, 893.
3.
Al-KaabiS. S., WilliamsD. H. L., BonnettR., and OoiS. L., J. Chem. Soc., Perkin Trans. 2, 1982, 227.
4.
(a) OaeS., ShinhamaK., Org. Prep. Proc. Int., 1983, 15, 165; (b) S. Monocada, R. M. J. Palmer and E. A. Higgs, Pharmacol. Rev., 1991, 43, 109; (c) P. L. Feldman, O. W. Griffith and J. Stuehr, Chem. Eng. News, 1993, 20, 26.
5.
CornelisA., DepayeN., GerstmansA., and LaszloP., Tetrahedron Lett., 1983, 24, 3103 and references cited therein.
6.
IranpoorN., FirouzabadiH., and ZolfigolM. A., Synth. Commun., 1998, 28, 367.
7.
FirouzabadiH., IranpoorN., and ZolfigolA., Synth. Commun., 1998, 28, 1179.
8.
(a) OaeS., FukushimaD., and KimY. H., J. Chem. Soc., Chem. Commun., 1977, 407; (b) Y. H. Kim, D. Shinhama and S. Oae, Tetrahedron Lett., 1978, 1211.
9.
RichardS., AudetP., and SavoieR., J. Mol. Struc., 1988, 178, 135.
10.
IranpoorN., FirouzabadiH., and HeydariR., Synth. Commun., 1999, in press.
11.
ZolfigolM. A., NematollahiD., and MallakpourS. E., Synth. Commun., 1999, 29, 2277.
