Reaktivität C‐arylierter cyclischer Maleinsäurehydrazide

Augustin, M.; Reinemann, Peter

doi:10.1002/zfch.19730130105

Cited by 5 publications

(3 citation statements)

References 7 publications

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“…Phenylthiourea VIc was described before [8], and the characteristics of compound we obtained were consistent with the published data…”

mentioning

confidence: 76%

“…On the other hand, Augustin and Reinemann who proved the possibility to obtain substituted azines from maleic and phthalic anhydrides assigned to the hydrazide of the endic anhydride the structure of aminoimide III [7]. Both viewpoint were further additionally supported [8][9][10][11] but strict proofs of the structure of hydrozinolysis product obtained from endic anhydride were lacking.…”

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confidence: 92%

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Structure and Reactivity of Bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboxylic (endic) Acid Hydrazide

et al. 2005

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Establishing of the structure of hydrazinolysis product obtained from bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboxylic (endic) acid was performed by preparation of the compound under alternative conditions followed by comparison of the characteristics and spectral parameters of the resulting substances, and also by quantum-chemical calculations by the density functional method of the chemical shifts in 1 H and 13 C NMR spectra of different reaction products. The X-ray diffraction analysis of the hydrazide was also carried out. The compound obtained was assigned a structure of N-aminobicyclo[2.2.1] hept-2-ene-endo-5,endo-6-dicarboximide. The products were prepared by its reactions with arylsulfonyl chlorides, benzoyl chlorides, m-tolyl and p-toluenesulfonyl isocyanates, phenyl isothiocyanate, with o-nitrobenzaldehyde, and oxiranes (1,2-epoxycyclohexane and 2,3-epoxypropylcarbazole). The aromatic sulfonamides, carboxamides, and ureas were epoxidized by performic acid obtained in situ from the formic acid and hydrogen peroxide. Products of [3+2]-cycloaddition of aryl azides to the strained double bond in the N-aminobicyclo[2.2.1] hept-2-ene-endo-5,endo-6-dicarboximide and its derivatives. The structures of compounds obtained were confirmed by their IR, 1 H and 13 C NMR spectra.

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“…Phenylthiourea VIc was described before [8], and the characteristics of compound we obtained were consistent with the published data…”

mentioning

confidence: 76%

mentioning

confidence: 92%

Structure and Reactivity of Bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboxylic (endic) Acid Hydrazide

et al. 2005

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“…(Scheme 37).Simmons and co-workers51a have reported the formation of a perfluoro derivative of bisazine, eicosafluoro-octahydro[1,1¢]bipiperidinyl (100) by the electrochemical fluorination of pyridine (99a) using hydrogen fluoride. An alternate method for the preparation of 100 (10%) involved irradiation of a mixture of perfluoro-N-chloropiperidine(101) and hexafluorocyclobutene(102). However, this reaction also yielded perfluoro-[N-(2-chlorocyclobutyl)piperidine] (103) as the major product (33%).…”

mentioning

confidence: 99%