Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2008
Selective Aerobic Oxidative Dibromination of Alkenes with Aqueous HBr and Sodium Nitrite as a Catalyst Ajda Podgoršek,a Marco Eissen,b Jens Fleckenstein,b Stojan Stavber,a Marko Zupana,c and Jernej Iskra*a a
Laboratory of Organic and Bioorganic Chemistry, ˝Jožef Stefan˝ Institute, Jamova 39, 1000 Ljubljana, Slovenia b Gymnasium Ganderkesee, Am Steinacker 12, 27777 Ganderkesee, Germany. c Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia
[email protected]
Supplementary Information NMR spectra of (2,3-dibromo-1,1,1-trifluoropropan-2-yl)benzene 20 .............................. 2 Figure 1: Environmental factor E of different bromination methods ................................. 3 UV-vis spectrum of Br2 in CH3CN..................................................................................... 4 UV-vis spectrum of NOBr .................................................................................................. 5
S1
Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2008
4.41 4.37 4.21 4.17
7.41
6.5
136
128
6.0
5.5
5.0
4.5 4.0 3.5 Chemical Shift (ppm)
96
88
80 72 64 56 Chemical Shift (ppm)
120
77.0
118.0
7.0
133.0 129.7 129.2 128.9 128.4 125.4 121.7
7.5
1.00
112
104
3.0
2.5
2.0
1.5
1.0
0.5
0
34.9
2.70
65.8 65.5
7.66
NMR spectra of (2,3-dibromo-1,1,1-trifluoropropan-2-yl)benzene 20
48
40
32
24
16
8
0
S2
Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2008
Figure 1: Environmental factor E of different bromination methods shown in Scheme 6 using the software EATOS.1 For details see Table 2. Work-up procedures have not been described in detail 2, 3 and, thus, were not considered here: (a) Recrystallization; b) Washing with water, brine and drying over sodium sulfate; c) Pouring into 10 mL of water
S3
Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2008
UV-vis spectrum of Br2 in CH3CN (2·10-3 M)
S4
Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2008
UV-vis spectrum of NOBr (NaNO2 and HBr in CH3CN (2·10-3 M))
References 1 M. Eissen, and J. O. Metzger, Chem. Eur. J. 2002, 8, 3580-3585. 2 N. B. Barhate, A. S. Gajare, R. D. Wakharkar and A. V. Bedekar, Tetrahedron, 1999, 55, 11127-11142. 3 H. G. O. Becker, in Organikum: Organisch-chemisches Grundpraktikum, WileyVCH, Weinheim, 21st ed., 2001, p. 299.
S5
