ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7

Published monthly
 

Ethynylation of diene adducts with methyl vinyl ketones and with N-substituted maleimides. Herbicide activity of final products

V. Sutoris and M. Furdík

Comenius University, Bratislava

 

Abstract: The synthesis of ethynylcarbinols by the ethynylation of the exocyclic ketones and bicyclic dicarboximides with Li-Al-acetylene complex in dry tetrahydrofuran and their herbicide activity was described. The exocyclic ketones were prepd. by Diels-Alder reaction of 1,3 dienes (cyclopentadiene, tetrachlorocyclopentadiene, hexachlorocyclopentadiene, isoprene and chloroprene) with H2C:CHCOMe. The following I were prepd. (R, R1, R2, R3, and b.p./torr given): H, H, H, C≡CH (Ia), 73-6°/2; H, H, H, Et, (Ib), 88°/9; H, Cl, Cl, C≡CH, 130-3°/1.5; Cl, Cl, Cl, Et, 153°/6; and the following II (R, R1 and b.p./torr given): Me, H (IIa), 84-6°/1.5; Me,COCH2Cl, 129°/1; Cl, H (IIb), 103-5°/3; Cl, COCH2Cl, 132°/1; and III, b. 60-2°/1 torr; and IV (R = iso-Pr), m. 168°, and IV (R = Ph), m. 192°. Ia was also prepd. by the Grignard reaction. It was detd. that the high yields 82-5% were obtained at the ethynylation of chloroprene and isoprene, which lack the endo-bridge causing the space obstruction. With the hexachloropentadiene contg. endo-dichloromethylene bridge, no ethynylated product was obtained either with Li-Al-acetylene complex or with the Grignard reaction. Herbicidal activity Ia compares favorably with 2,4-D; it decreases in the order: IIa, III, Ib, IIb. The phytotoxic effect on the agricultural plants is discussed. 5 tables are given.

Full paper in Portable Document Format: 215a329.pdf (in Slovak)

 

Chemical Papers 21 (5) 329–339 (1967)

Thursday, March 28, 2024

IMPACT FACTOR 2021
2.146
SCImago Journal Rank 2021
0.365
SEARCH
Advanced
VOLUMES
European Symposium on Analytical Spectrometry ESAS 2022
© 2024 Chemical Papers