5585-23-9Relevant academic research and scientific papers
Unexpectedly Stable (Chlorocarbonyl)(N-ethoxycarbonylcarbamoyl)disulfane, and Related Compounds That Model the Zumach-Weiss-Kühle (ZWK) Reaction for Synthesis of 1,2,4-Dithiazolidine-3,5-diones
Barany, George,Britton, Doyle,Chen, Lin,Hammer, Robert P.,Henley, Matthew J.,Schrader, Alex M.,Young, Victor G.
, p. 11313 - 11321 (2015/12/01)
The Zumach-Weiss-Kühle (ZWK) reaction provides 1,2,4-dithiazolidine-3,5-diones [dithiasuccinoyl (Dts)-amines] by the rapid reaction of O-ethyl thiocarbamates plus (chlorocarbonyl)sulfenyl chloride, with ethyl chloride and hydrogen chloride being formed as coproducts, and carbamoyl chlorides or isocyanates generated as yield-diminishing byproducts. However, when the ZWK reaction is applied with (N-ethoxythiocarbonyl)urethane as the starting material, heterocyclization to the putative "Dts-urethane"? does not occur. Instead, the reaction directly provides (chlorocarbonyl)(N-ethoxycarbonylcarbamoyl)disulfane, a reasonably stable crystalline compound; modified conditions stop at the (chlorocarbonyl)[1-ethoxy-(N-ethoxycarbonyl)formimidoyl]disulfane intermediate. The title (chlorocarbonyl)(carbamoyl)disulfane cannot be converted to the elusive Dts derivative, but rather gives (N-ethoxycarbonyl)carbamoyl chloride upon thermolysis, or (N-ethoxycarbonyl)isocyanate upon treatment with tertiary amines. Additional transformations of these compounds have been discovered, providing entries to both known and novel species. X-ray crystallographic structures are reported for the title (chlorocarbonyl)(carbamoyl)disulfane; for (methoxycarbonyl)(N-ethoxycarbonylcarbamoyl)disulfane, which is the corresponding adduct after quenching in methanol; for [1-ethoxy-(N-ethoxycarbonyl)formimidoyl](N′-methyl-N′-phenylcarbamoyl)disulfane, which is obtained by trapping the title intermediate with N-methylaniline; and for (N-ethoxycarbonylcarbamoyl)(N′-methyl-N′-phenylcarbamoyl)disulfane, which is a short-lived intermediate in the reaction of the title (chlorocarbonyl)(carbamoyl)disulfane with excess N-methylaniline. The new chemistry and structural information reported herein is expected to contribute to accurate modeling of the ZWK reaction trajectory.
INSECTICIDAL AND NEMATICIDAL DIFLUOROALKENE DERIVATIVES
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Page/Page column 29, (2008/06/13)
Disclosed are compounds of Formula I, and their N-oxides and suitable salts thereof, which are useful for controlling invertebrate pests. I wherein Q is Q-1 or Q-2; Y is H, F, Cl or CH3; A is CN, C1-C6 alkyl, ORla, SRla, NRlaR2a or CONR1bR2b; Z is O, S or NR3; W is N or CR4; and J1, J2, Rla, R2a, R1b, R2b, R3, R4, R10 and n are as defined in the disclosure. Also disclosed are methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula I, an N-oxide thereof or a suitable salt of the compound (e.g., as a composition described herein). This invention also pertains to a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula I, anN-oxide thereof or a suitable salt of the compound and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent.
A new route to 2-oxazolines, bis-oxazolines, and 2-Imidazoline-5-ones from imidates using solvent-free cycloadditions: Synthesis, chemical properties, and PM3 MO calculations
Lerestif, Jean Michel,Toupet, Loic,Sinbandhit, Sourisak,Tonnard, Francois,Bazureau, Jean Pierre,Hamelin, Jack
, p. 6351 - 6364 (2007/10/03)
The 1,3-dipolar cycloadditions between imidate 1, derived from dimethylaminomalonate and aldehydes 2(a-f), phthalaldehyde 2g, isophthalaldehyde 2h. 4-chlorophenylisocyanate 9a, ethoxycarbonylisothiocyanate 9d as dipolarophiles proceeds regioselectively in
