774
NEDOLYA et al.
1
measuring scale was 100/100 cm , scanning time
11 min. The resolution of the spectrometer in 1700
sive Organic Chemistry, Sutherland, I.O., Ed.,
Pergamon Press, Oxford, 1979.
9. Nedolya, N.A. and Trofimov, B.A., Sulfur Reports,
1994, vol. 15, no. 2, pp. 237 316.
1
1
1500 and 3500 3200 cm regions was 1 and 2 cm
respectively. H and 13C NMR spectra were recorded
on spectrometer Bruker DPX-400 (400 and 100 MHz
respectively, 5 10% solution in CDCl3) at room
temperature, internal reference HMDS.
1
10. Nedolya, N.A. and Trofimov, B.A., Sulfur Reports,
1994, vol. 15, no. 3, pp. 339 380.
11. Nedolya, N.A., Brandsma, L., Zinov,eva V.P., Tro-
fimov, B.A., Zh. Org. Khim., 1997, vol. 33, no. 1,
pp. 91 96.
2-(Vinyloxy)ethyl isothiocyanate (I) was synthesiz-
ed by method [26], the dicarboxylic acids used were
commercial products purified by recrystallization.
N1,N3-Bis[2-(vinyloxy)ethyl]malonamide (III),
N1, N4-bis[2-(vinyloxy)ethyl]succinamide (IV),
N1,N5-bis[2-(vinyloxy)ethyl]pentanediamide (V),
N1,N6-bis[2-(vinyloxy)ethyl]hexanediamide (VI),
N1,N7-bis[2-(vinyloxy)ethyl]heptanediamide (VII),
N ,N -bis[2-(vinyloxy)ethyl]decanediamide (VIII)
and N1,N2-bis[2-(vinyloxy)ethyl]phthalamide (X)
were prepared under conditions indicated in Table 1.
As a rule, a calculated amount of dicarboxylic acid
was added to the stirred solution of triethylamine
(10 15 wt%) in 2-(vinyloxy)ethyl isothiocyanate (I).
In the synthesis of amides III and X was used a 50%
excess of isothiocyanate (I) over the stoichiometric
amount. The reaction products were purified by
reprecipitation with hexane from acetone solution.
12. Nedolya, N.A., Brandsma, L., Zinov,eva, V.P., and
Trofimov, B.A., Zh. Org. Khim., 1998, vol. 34,
no. 10, pp. 1559 1564.
13. Nedolya, N.A., Novel Chemistry Based on Isothio-
cyanates and Polar Organometallics, PhD. Thesis
(Utrecht University, The Netherlands), 1999, 144 p.
14. Brandsma, L., Nedolya, N.A., Tarasova, O.A., and
Trofimov, B.A., Khim. Geterotsikl. Soed., 2000,
no. 11, pp. 1443 1463.
15. Brandsma, L., Tolmachev, S.V., and Nedolya, N.A.
Abstracts of Papers, Eurasian Conference on Hetero-
cyclic Compounds, Suzdal, 2000, p. 44.
16. Nedolya, N.A., Papsheva, N.P., Afonin, A.V., and
Trofimov, B.A., Zh. Org. Khim., 1991, vol. 27,
no. 10, pp. 2239 2241.
1
1
0
17. Nedolya, N.A., Papsheva, N.P., Afonin, A.V., Tro-
fimov, B.A., Kukhareva, V.A., and Kashik, T.V.,
Izv. Akad. Nauk SSSR, Ser. Khim., 1991, no. 10,
pp. 2370 2372.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 2 2002