Short Communication
2115
3
1
an oil which was shown to contain only hexamethylphosphortriamide ( P NMR δ = +24 ppm) and
VIa. The former was removed by distillation at 60 °C/0.657 Pa whereby the latter remained; yield 59 mg
(
62.3%), m.p. 62 – 64 °C (hexane). For C H N O (146.1) calculated: 65.75% C, 4.12% H, 19.17% N;
8 6 2
1
found: 65.55% C, 4.07% H, 19.03% N. IR spectrum (KBr): 2 225 (CN), 1 610 (C=C, furan). H NMR
spectrum (CDCl ): 3.26 d, 2 H, J(H,H) = 8 (CH ); 3.91 t, 1 H, J(H,H) = 8 (CH); 6.4 – 7.8 m, 3 H (furan).
3
2
+
Mass spectrum, m/z: 146 (M , 100%).
Reaction of Va with Hydrogen Chloride
A stirred suspension of Va in CH Cl (20 ml) was cooled to 0 – 5 °C and treated with anhydrous HCl
2
2
gas to saturation. The red solution became yellow; after 15 min the solvent was removed at 2 368 Pa.
The solid (224 mg, 90%) of the aminophosphonium salt VIIa was obtained, m.p. 183 °C (ethanol).
For C H ClN OP (343.8) calculated: 48.90% C, 6.74% H, 10.31% Cl, 20.37% N, 9.01% P; found:
1
4
23
5
1
4
8.86% C, 6.35% H, 10.08% Cl, 20.25% N, 9.27% P. H NMR spectrum (CDCl ): 4.2 dd, 1 H
J(H,P) = 23.5, J(H,H) = 13.5 (CH−P); 4.55 dd, 1 H, J(H,P) = 10.5, J(H,H) = 13.5 (C−CH); 6.4 – 7.8 m,
H (furan). P NMR spectrum (CDCl ): 52.5. Mass spectrum, m/z: 343 (M , 55%).
3
2
3
3
1
+
3
3
Wittig Reaction of Compound Va
A solution of Va (0.2 g) in ethyl acetate (25 ml) was heated under reflux with benzaldehyde (2 ml)
for 8 h. The precipitate formed on cooling was washed with cold benzene and then recrystallized
from benzene to give VIII (100 mg, 67%), m.p. 176 °C. For C H N O (234.3) calculated: 76.91% C,
1
5
10
2
4
.30% H, 11.96% N; found: 76.82% C, 4.18% H, 11.09% N. IR spectrum (KBr): 2 230 (CN), 1 618
1
(
C=C), 1 600 (arom.). H NMR spectrum (CDCl ): 4.05 d, 1 H, J(H,H) = 4 (CHCN); 5.65 d, 1 H,
3
+
J(H,H) = 4 (C=CH−Ph); 6.2 – 8.15 m, 9 H (furan and arom.). Mass spectrum, m/z: 234 (M , 100%).
REFERENCES
1. Abou W. M., Khidre M. D., Mahran M. R.: J. Prakt. Chem. 332, 1029 (1990).
2. Mahran M. R., Abdou W. M., El-Rahman N. A. A., Khidre M. D.: J. Heteroatom. Chem. 3, 93
(
1992).
3
4
5
6
7
8
. Hudson R. F., Chopard P. A.: Helv. Chim. Acta 46, 2178 (1963).
. Ramirez F., Madan O. P., Smith C. P.: Tetrahedron 22, 567 (1966).
. Burgada R.: C. R. Acad. Sci., 2 268, 1310 (1969).
. Ramirez F., Patwardhan A. V., Kugler H. J., Smith C. P.: J. Am. Chem. Soc. 89, 6276 (1967).
. Mark V.: J. Am. Chem. Soc. 85, 1884 (1963).
. Cadogan J. I. G.: Organophosphorus Reagents in Organic Synthesis. Academic Press, London
1
979; and references therein.
9. Newmann M. S., Blum S.: J. Am. Chem. Soc. 86, 5598 (1964).
1
1
1
1
0. Abdou W. M., Ganoub N. A. F., Mahran M. R.: Bull. Chem. Soc. Jpn. 64, 747 (1991).
1. Burgada R., Leroux Y., El-Khoshnieh Y. O.: Tetrahedron Lett. 21, 925 (1980).
2. Heuck R.: Chem. Ber. 28, 2253 (1985).
3. Schneller S. W., Moore D. R.: J. Org. Chem. 40, 1840 (1975).
Collect. Czech. Chem. Commun. (Vol. 59) (1994)