REACTION OF UNSATURATED ESTERS WITH THE OXIDATIVE SYSTEM
1229
formed in the flask. In the condensed solvent we
Zaburdaeva, M.A., Zh. Obshch. Khim., 1994, vol. 64,
found 1.65 g of t-BuOH, 0.30 g of allyl acetate,
no. 10, pp. 1715 1721.
0
.27 g of tert-butyl peroxyacetate, and 0.02 g of
1
1
0. Stepovik, L.P., Zaburdaeva, M.A., and Dodono-
va, V.A., Zh. Obshch. Khim., 1997, vol. 67, no. 1,
pp. 116 120.
acrolein. The condensates obtained in several runs
were treated with 2,4-dinitrophenylhydrazine to obtain
acrolein 2,4-dinitrophenylhydrazone, mp 168 C.
Mixed mp 169 C.
1. Takai, K., Oshima K., and Nozaki, N., Bull. Chem.
Soc. Jpn., 1983, vol. 56, no. 12, pp. 3791 3795.
The residue was hydrolyzed with 10% H SO ,
12. Takai, K., Oshima K., and Nozaki N., Tetrahedron
Lett., 1980, vol. 21, no. 17, pp. 1657 1660.
2
4
extracted with ether, and dried with sodium sulfate.
In the acidic aqueous solution we found 0.26 g of
t-BuOH and 0.19 g aluminum, and in the ether extract,
.25 g of t-BuOH, 0.11 g of t-BuOOH, and 0.075 g
of (hydroxymethyl)oxirane. In the course of hydro-
1
1
1
1
1
1
3. Dodonov, V.A., Stepovik, L.P., and Sofronova, S.M.,
Zh. Obshch. Khim., 1981, vol. 51, no. 12, pp. 2730
0
2
735.
4 Stepovik, L.P., Zaburdaeva, M.A., and Dodonov, V.A.,
lysis, 0.016 g of CO was liberated, which was deter-
3
Zh. Obshch. Khim., 1997, vol. 67, no. 7, pp. 1173
mined as barium carbonate (0.072 g). In a parallel
experiment, by the same procedure we found 0.105 g
of acetic acid, 0.08 g of acrylic acid, 0.07 g of allyl
alcohol (as 0.13 g of allyl acetate after treatment of
the dry residue with acetic anhydride in benzene).
1
178.
5. Stepovik, L.P., Sofronova, S.M., Dodonova, V.A., and
Pomoshnikova, T.V., Zh. Obshch. Khim., 1985,
vol. 55, no. 7, pp. 1561 1565.
6. Razuvaev, G.A., Stepovik, L.P., and Mitrofano-
va, M.V., Zh. Obshch. Khim., 1965, vol. 35, no. 6,
pp. 1095 1098.
Hydromethyloxirane in the hydrolyzate was quali-
tatively confirmed by the periodic acid test for the
oxirane ring [24].
7. Stepovik, L.P., Martynova, I.M., and Dodonov, V.A.,
Zh. Obshch. Khim., 2001, vol. 71, no. 11, pp. 1905
1910.
The reaction of methyl acrylate with system I + II
and products analysis were carried out in a similar
way.
8. Bauer, K.H., Die organische Analyse, Leipzig, 1950.
Translated under the title Analiz organicheskikh soe-
dinenii, Moscow: Inostrannaya Literatura, 1953,
p. 234.
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 72 No. 8 2002