H. W o jtowicz et al. / Tetrahedron 57 ꢀ2001) 9743±9748
9747
with tert-butyl hydroperoxide in the same manner as
described in Section 4.2, and the reaction was continued
for 180 h. After this period, the solvent was evaporated in
vacuo and the products were isolated on silica gel column.
The esters 5b and 6b were eluted with chloroform±hexane
yield 0.735 g ꢀ73%), mp 194±2008C ꢀdecomposition)
ꢀfound: C, 46.27, H, 4.02, Cl, 8.10, N, 6.43.
C H ClN O Se requires: C, 46.01, H, 3.86, Cl, 7.99, N,
1
7
17
2
5
6.31%). nmax ꢀKBr) 3243±2868 ꢀOH, CH), 1621 ꢀCO),
1550, 1342 ꢀNO ), 858, 837 ꢀSeO) cm ; d ꢀDMSO-d6),
2
1
2
H
ꢀ
2:1) and then acid 2b was eluted with acetone. In another
experiment, the reaction mixture was hydrolyzed with
0% sulfuric acid ꢀ35 ml) at 1008C for 1 h. The formed
solid, ®ltered off and dried in air was pure acid 2b ꢀyield
1.09 ꢀs, 9H, CH ), 7.53 ꢀd, 2H, J9.0 Hz, ArH), 7.58 ꢀd, 2H,
3
J9.0 Hz, ArH), 8.52 ꢀd, 2H, J8.1 Hz, ArH), 8.70 ꢀdd, 1H,
J8.1 and 2.1 Hz, ArH), 10.73 ꢀbs, 1H, OH).
7
8
9%).
Acknowledgements
4
4
.3.1. tert-Butyl 4-nitrobenzoate ꢀ5b). White prisms, yield
9%, mp 114±1168C, Ref. 25 115±1168C.
This work was supported by the Polish State Committee for
scienti®c research ꢀGrant No. TO9A 097 17).
4.3.2. Peroxy-tert-butyl 4-nitrobenzoate ꢀ6b). White
prisms, yield 19%, mp 71±748C, Ref. 26 68±708C.
References
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selenazol-3ꢀ2H)-one ꢀ10) with hydrogen peroxide
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ꢀ
100 ml) was added dropwise, over 1 h with vigorous
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.00, N, 6.70%; C H ClN O Se requires: C, 38.68, H,
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2
2
1
ꢀ
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H 6
2
H, J8.8 Hz, ArH), 7.58 ꢀd, 2H, J8.8 Hz, ArH), 8.52
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0. Back, T. G. In Organoselenium Chemistry, Back, T. G., Ed.;
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butyl hydroperoxide ꢀ10 ml) which was cooled on an ice/
salt bath. The reaction was continued for an additional 1.5 h
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®
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