1644
E. V. Sharova et al. / Tetrahedron Letters 49 (2008) 1641–1644
5. Artyushin, O. I.; Sharova, E. V.; Odinets, I. L.; Lenevich, S. V.; acid 3 is insoluble in phosphonium and imidazolium tetrafluoroborate
Morgalyuk, V. P.; Tananaev, I. G.; Pribulova, G. V.; Myasoedova, G.
V.; Mastryukova, T. A.; Myasoedov, B. F. Russ. Chem. Bull. 2004,
ionic liquids even at 100 °C. In these cases, acetonitrile was used as a
co-solvent (100 vol %). Addition of this co-solvent had no detrimental
effect on the yield and reaction rate in the case of other ionic liquids.
The mixture was heated at 100–110 °C and then allowed to cool to
53, 2499.
6
. (a) Arnaud-Neu, F.; B o¨ hmer, V.; Dozol, J.-F.; Gr u¨ ttner, C.; Jakobi,
R. A.; Kraft, D.; Mauprivez, O.; Rouquette, H.; Schwing-Weill, M.-J.;
Simon, N.; Vogt, W. J. Chem. Soc., Perkin Trans. 2 1996, 1175; (b)
Babain, V. A.; Alyapyshev, M. Yu.; Caravan, M. D.; B o¨ hmer, V.;
Wang, L.; Shokova, E. A.; Motornaya, A. E.; Vatsouro, I. M.;
Kovalev, V. V. Radiochim. Acta 2005, 93, 749; (c) Peters, M. W.;
Werner, E. J.; Scott, M. J. Inorg. Chem. 2002, 41, 1707.
room temperature. Compound 4a obtained from [P(C
compound 4b obtained from [P(C (C14 29)]BF
tated by the addition of 20 ml of Et O/MeOH (95:5) followed by
filtration and drying in vacuo. Compound 4a obtained from
[bmim]Br, and compound 4b obtained from [bmim]Br and [bmim]PF
8
H
17
)
4
]Br and
6
H
13
)
3
H
4
were precipi-
2
6
were precipitated by the addition of water (10 ml). Dibutylamide 4d
was isolated by extraction with diethyl ether (3 Â 10 ml) followed by
solvent evaporation.
7
8
9
. Schvezov, I. K.; Truchlyaev, P. S.; Kalistratov, V. A.; Kulashko, V.
G.; Kharitonov, A. V.; Antoshin, A. E.; Tsvetkov, E. N. Radiokhim.
1
989, 63.
(b) To a mixture of 253 mg (1.15 mmol) of [bmim]Br, 0.3 g
. Artyushin, O. I.; Sharova, E. V.; Odinets, I. L.; Lyssenko, K. A.;
Golovanov, D. G.; Mastryukova, T. A.; Pribulova, G. A.; Tananaev,
I. G.; Myasoedova, G. V. Russ. Chem. Bull. 2006, 55, 1440.
. Ionic Liquids as Green Solvents: Progress and Prospects; Rogers, R.
D., Seddon, K. R., Eds.; ASC Symposium Ser.: Washington, DC,
(1.15 mmol) of 3, 1.2 mmol of the corresponding amine and 15 ml
of toluene or dibutyl ether as a second-phase after dilution of the
phosphorus substrate as described above, 109 mg (0.35 mmol) of
triphenyl phosphite was added at ꢁ50 °C. The mixture was heated for
40 min–2.5 h as appropriate, cooled to room temperature and the
layers were separated. The solvent layer was evaporated to dryness to
afford the final product having purity >95% according to NMR data.
In the recycling experiments, reactants were added to the ionic liquid
solution remaining in the reaction vessel to start the next run. Similar
results were obtained using 0.1 mol of phosphorus substrate, indicat-
ing the possibility of further scaling up if necessary. Compounds
2
003.
1
1
0. Keglevich, G.; Baan, Z.; Finta, Z.; Hermecz, I.; Novak, T.; Odinets, I.
L. Curr. Org. Chem. 2007, 11, 107.
1. (a) Kryshtal, G. V.; Zhdankina, G. M.; Zlotin, S. G. Mendeleev
Commun. 2002, 176; (b) Lee, S.-gi.; Park, J. H.; Kang, J.; Lee, J. K.
Chem. Commun. 2001, 1698; (c) Yadav, J. S.; Reddy, B. V. S.;
Sreedhar, P. Green Chem. 2002, 4, 436; Yoshino, T.; Imori, S.; Togo,
H. Tetrahedron Lett. 2006, 62, 1309; (d) Matveeva, E. V.; Odinets, I.
L.; Kozlov, V. A.; Shaplov, A. S.; Mastryukova, T. A. Tetrahedron
Lett. 2006, 47, 7645.
8
5
2a
4a,b, 4c and 4d are known and after isolation, their physicochem-
ical constants and spectral data compared well with the literature
data. Conversion was determined by integration of the signals in the
3
1
31
3 4
P NMR spectra [85% H PO ( P) as an external standard].
1
2. General procedure: (a) A mixture of an ionic liquid (3 g), 1.2 mmol of
the corresponding amine and 0.3 g (1.15 mmol) of diphenylphos-
phorylacetic acid 3 was heated to ꢁ100 °C under stirring. After
dissolution of the starting substrates (ca. 5 min), the mixture was
cooled to 50 °C and 358 mg (1.15 mmol) of triphenyl phosphite was
added. It should be noted that the starting diphenylphosphoryl acetic
13. Crowhurst, L.; Lancaster, N. L.; P e´ rez Arlandis, J. M.; Welton, T. J.
Am. Chem. Soc. 2004, 126, 11549.
14. (a) Visser, A. E.; Rogers, R. D. J. Solid State Chem. 2003, 171, 109;
(b) Molochnikova, N. P.; Pribylova, G. A.; Zakharchenko, E. A.;
Myasoedova, G. V. Proceedings of XVIII Mendeleev Conference of
General and Applied Chemistry 2007, 5, 311.