6216
A. Chrobok / Tetrahedron 66 (2010) 6212e6216
acetate (bmimBF
trated, dried under vacuum (60 C, 5 h) and reused.
4
) or dibutyl ether (HmimOAc), ILs were concen-
Supplementary data
ꢀ
4
.4. Stability of OxoneÒ
A solution of OxoneÒ (0.63 g) in 0.7 g of IL was stirred for 5 h at
ꢀ
4
0 C. After this time the content of KHSO
5
was determined by
References and notes
iodometric titration.
.5. Solubility of OxoneÒ
1. Baeyer, A.; Villiger, V. Ber. Dtsch. Chem. Ges. 1899, 32, 3625e3633.
4
2. (a) Krow, G. Org. React. 1993, 43, 251e798; (b) Renz, M.; Meunier, B. Eur. J. Org.
Chem. 1999, 737e750.
3. (a) Strukul, G. Angew. Chem., Int. Ed. 1998, 37, 1198e1209; (b) Brink, G.; Arends,
I.; Sheldon, R. A. Chem. Rev. 2004, 104, 4105e4123.
OxoneÒ (4 g) was mixed with 5 g of IL and stirred for 1 h at room
temperature. Next, CH
2
Cl
2
was added to isolate the insoluble parts
4
. (a) Gonzalez-Nunez, M. E.; Mello, R.; Olmos, A.; Asensio, G. J. Org. Chem. 2005,
Ò
of Oxone and to lower the viscosity. The mixture was filtered and
70, 10879e10882; (b) Gonzalez-Nunez, M. E.; Mello, R.; Olmos, A.; Asensio, G. J.
the amount of KHSO
titration.
5
in the filtrate was determined by iodometric
Org. Chem. 2006, 71, 6432e6436.
. (a) Yang, D. Acc. Chem. Res. 2004, 37, 497e505; (b) Travis, B. R.; Sivakumar, M.;
Hollist, G. O.; Borhan, B. Org. Lett. 2003, 5, 1031e1034.
5
6
. Wasserscheid,P.;Welton, T. IonicLiquids inSynthesis; Wiley-VCH:Weinheim,2007.
4
.6. Analysis
7. (a) Gupta, N.; Sonu; Kad, G. L.; Singh, J. Catal. Commun. 2007, 8, 1323e1328; (b)
Hajipour, A. R.; Rajaei, A.; Ruoho, A. E. Tetrahedron Lett. 2009, 50, 708e711; (c)
Khosropour, A. R. Can. J. Chem. 2008, 86, 264e269; (d) Xu, D. Q.; Yang, W. L.;
Luo, S. P.; Wang, B. T.; Wu, M.; Xu, Z. Y. Eur. J. Org. Chem. 2007, 1007e1012; (e)
Wang, W.; Cheng, W.; Shao, L.; Yang, J. Catal. Lett. 2008, 121, 77e80; (f) Du, Y.;
Tian, F.; Zhao, W. Synth. Commun. 2006, 36, 1661e1669.
8. (a) Baj, S.; Chrobok, A. Synth. Commun. 2008, 38, 1e7; (b) Baj, S.; Chrobok, A.;
S1upska, R. Green Chem. 2009, 11, 279e282; (c) Chrobok, A.; Baj, S.; Pudlo, W.;
Jarzebski, A. Appl. Catal., A 2009, 366, 22e28.
All products were characterized by comparing their NMR
spectra with these of authentic samples: -valerolactone, -capro-
lactone, 2-oxabicyclo[3.2.1]octan-3-one, 4-oxatricyclo [4.3.1.13,8]
d
e
4
b
undecan-5-one, phenyl acetate, butyl acetate,
6-methyl-
4-methoxyphenyl ace-
caprolactone,1 3,4-dihydrocoumarin,
7a
17b
17c
9
. Kennedy, R. J.; Stock, A. M. J. Org. Chem. 1960, 25, 1901e1906.
10. Xu, W.; Cooper, E. I.; Angell, C. A. J. Phys. Chem. B 2003, 107, 6170e6178.
1. Greaves, T. L.; Drummond, C. J. Chem. Rev. 2008, 108, 206e237.
tate, tert-butyl acetate, isopropyl acetate.
H NMR and C NMR spectra were recorded at 300 MHz in
CDCl (Varian Unity Inova plus, internal TMS). GC analysis was
performed using a PerkineElmer chromatograph and decane as the
external standard. HPLC (Alliance, Waters 2690 system) was per-
1
13
1
3
12. Kosmulski, M.; Marczewska-Boczkowska, K.; Zukowski, P.; Subocz, J.; Saneluta,
C. Croat. Chem. Acta 2007, 80, 461e466.
13. Crosthwaite, J. M.; Muldoon, M. J.; Dixon, J. K.; Anderson, J. L.; Brennecke, J. F. J.
Chem. Thermodyn. 2005, 37, 559e568.
14. Bonhote, P.; Dias, A. P.; Papageorgiou, N.; Kalyanasundaram, K.; Graetzel, M.
formed using a 2ꢁ150 mm column (Nova-Pak Silica, 60A, 4
and a solvent system of hexane/2-propanol (95/5 v/v, flow rate
.25 ml/min).
mm)
Inorg. Chem. 1996, 35, 1168e1178.
1
5. Gomez, E.; Gonzalez, B.; Calvar, N.; Tojo, E.; Dominguez, A. J. Chem. Eng. Data
006, 51, 2096e2102.
6. Shang, H.; Wu, J.; Zhou, Q.; Wang, L. J. Chem. Eng. Data 2006, 51,
1286e1288.
7. (a) Jacobson, S. E.; Mares, F.; Zambri, P. M. J. Am. Chem. Soc. 1979, 101,
938e6946; (b) Zeitler, K.; Rose, C. A. J. Org. Chem. 2009, 74, 1759e1762; (c)
0
2
1
Acknowledgements
1
6
This work was financially supported by the Ministry of Science
Spectral Database for Organic Compoundsdinternet site organized by National
and Higher Education (Grant no N N209 149236).
Institute of Advanced Industrial Science and Technology, Japan.