Dimethoxycarben (1) addiert an Fumar- oder Maleinester unter Bildung von 3,3-Dimethoxy-cyclopropan-trans-1,2-dicarbonester (6). Bei der Addition an Styrol-Derivate entstehen ebenfalls 3,3-Dimethoxycyclopropane, wahrend mit Acetylendicarbonester, Phenylacetylen oder Diphenylketen 1:2-Addukte unterschiedlicher Struktur resultieren.



Carbene Reactions, IV. Addition of Dimethoxycarbene to CC Multiple Bonds



Dimethoxycarbene (1) adds to diethyl fumarate or maleate to form diethyl 3,3-dimethoxycyclopropane-trans-1,2-dicarboxylate (6). Addition to styrene derivatives yields similarly 3,3-dimethoxycyclopropanes, whereas addition to acetylenedicarboxylate, phenylacetylene or diphenylketene led to 1:2-adducts of varying structure.

Carben-Reaktionen, IV. Addition von Dimethoxycarben an CC-Mehrfachbindungen

1-Cyclohexyl-2-cyclohexylaminomethylene-4,5-diphenyl-1,2-dihydropyrrol-3-one 4a and 1-aryl-2-arylaminomethylene-4,5-diphenyl-1,2-dihydropyrrol-3-ones 4b,c as the E-form are synthesized by the reaction between N,N′-dicyclohexylethane-1,2-diylidenediamine 2a and N,N′-diarylethane-1,2-diylidenediamines 2b,c with diphenylcyclopropenone 1 through a formal [2 + 3] cycloaddition reaction. The structure assignment of 4a is confirmed on the basis of an X-ray crystal-structure determination. Similarly, diaryl azines 8a–c react with 1 through a formal [2 +
3] cycloaddition reaction to give the non-isolable product Δ4-pyrrolin-3-ones 10a–c which undergo oxidative rearrangement to afford ultimately the indenone derivatives 9a–c.

Reaction of diimines and azines with diphenylcyclopropenone

Microwave-assisted synthesis of 2-styryl-1,3,4-oxadiazoles from cinnamic acid hydrazide and triethyl orthoesters

The chemical properties of organic compounds containing an open-chain hydrazono-group are surveyed systematically. A list of 412 references is included.

https://iopscience.iop.org/article/10.1070/RC1972v041n06ABEH002071/pdf

The Reactions of Hydrazones

Reactions of o-aminothiophenol withαβ-unsaturated dicarbonyl systems. Facile synthesis of benzothiazines and benzothiazepines

Neuartige spiroverbindungen durch addition von maleinimiden an schiff-basen

The synthesis of a 1, 5-diphenyl perhydro-pyrazolo-[1, 2-a] pyrazole (IV) (m. p. = 170–171°) by LiAlH4-reduction of its 3, 7-dioxo derivative Va, one of the stereoisomers of V, is described. Va was obtained in small yield by the reaction of cinnamic acid with its hydrazide or with hydrazine. It proved to be identical with the compound obtained previously by interaction of cinnamic acid hydrazide with iodine which in the literature erroneously had been described as N, N′-dicinnamoyl hydrazine. This hydrazine now was obtained by bis-acylation of hydrazine with cinnamoyl chloride.



In Va the extremely low NMR. absorption of the tertiary protons at ρ = 4,6 ppm is probably due to the spatial grouping 






with the proton situated in the deshielding region of the carbonyl group.



Previously, another tertiary proton with a very low NMR. absorption at ρ = 4,85 ppm has been observed in the «bisimide M», the main criss-cross addition product of one mole benzaldazine and two moles of N-(n-butyl)-maleinimide. A stereostructure for bisimide M is now proposed, which is a hybrid between those of the bisimides L and H.

L. Zirngibl

Papers

Neuartige spiroverbindungen durch addition von maleinimiden an schiff-basen

Über 1, 5‐Diphenyl‐2, 3, 6, 7‐tetrahydro‐1H, 5H‐pyrazolo[1, 2‐a]pyrazole(2, 6‐Diphenyl‐1, 5‐diazabicyclo[3, 3, 0]octane)

Umsetzungen des 16α, 17α-epoxy-16β-methylpregnenolons mit ammoniak und primaeren aminen

Neuartige spiroverbindungen durch addition von maleinimiden an schiff-basen