CHEMICAL AND PHYSICAL PROPERTIES OF (Z)—AND (E) -MONOETHOXY-1-(2-NITRO-1-PROPENYL) BENZENES: Important Precursors to the monoethoxyamphetamines

Arnold W. By Research scientist, Drug Identification Division, Bureau of Drug Research, Health Protection Branch, Health and Welfare Canada. Tunney's Pasture, Ottawa, Ontario, Canada, K1A 0L2.

Bruce A. Lodge Head, Chemistry section, Drug Identification Division, Bureau of Drug Research, Health Protection Branch, Health and Welfare Canada. Tunney's Pasture, Ottawa, Ontario, Canada, K1A 0L2.

Wing-Wah Sy Research scientist, Drug Identification Division, Bureau of Drug Research, Health Protection Branch, Health and Welfare Canada. Tunney's Pasture, Ottawa, Ontario, Canada, K1A 0L2.

Jiri Zamecnik Research scientist, Drug Identification Division, Bureau of Drug Research, Health Protection Branch, Health and Welfare Canada. Tunney's Pasture, Ottawa, Ontario, Canada, K1A 0L2.

Randy Duhaime Technologist, Drug Identification Division, Bureau of Drug Research, Health Protection Branch, Health and Welfare Canada. Tunney's Pasture, Ottawa, Ontario, Canada, K1A 0L2.

ABSTRACT

(Z)-Monoethoxy-1- (2-nitro-1-propenyl)benzenes were synthesized from the corresponding (E)-isomers by irradiation with light in toluene in the presence of benzophenone. The gas-liquid chromatographic (GLC) and thin-layer chromatographic (TLC) data, and ultraviolet (UV), infrared (IR), proton magnetic resonance (¹H-NMR), and mass spectra (MS) are presented for both isomers for comparison. The (Z)-isomer is partially converted on the injector of GLC apparatus to the (E)-isomer.

RÉSUMÉ

Les (Z)-monéthoxy-1-(2-nitro-1-propényl)benzènes ont été synthétisés à partir des isomères-(E) correspondants par irradiation à la lumière dans le toluène avec de la benzophénone. Les données de chromatographie gaz-liquide (CGL), de chromatographie en couche mince (CCM) et les spectres d'ultraviolet (UV), d'infrarouge (IR) et de résonance magnétique nucléaire du proton (RMN-¹H) ainsi que les spectres de masses sont présentés pour les deux isomères pour en faire le comparaison. Il y a une conversion partielle de l'isomère-(Z) à la configuration (E) dans le port de l'injection de l'appareil de CGL.

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CHEMICAL AND PHYSICAL PROPERTIES OF (Z)—AND (E) -MONOETHOXY-1-(2-NITRO-1-PROPENYL) BENZENES: Important Precursors to the monoethoxyamphetamines

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CHEMICAL AND PHYSICAL PROPERTIES OF (Z)—AND (E) -MONOETHOXY-1-(2-NITRO-1-PROPENYL) BENZENES: Important Precursors to the monoethoxyamphetamines

ABSTRACT

RÉSUMÉ

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