Conclusions
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1.
When benzylidene- and alkylideneallylamines are heated in contact with oxide catalysts the C=C bond undergoes shift to respectively give the conjugated system C6H5CH=NCH=CHCH3 and RCH=NCH =CHCH3. The optimum conditions for this isomerization are an aluminum-chromium-potassium catalyst and a temperature of 250°.
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2.
A study was made of the isomerization of aralkyl imines with substituents in the benzene ring, RC6H4CH=NCH2CH=CH2. In their effect on the shift of the C=C bond from the allyl to the propenyl position the substituents can be arranged in the order: p-CH3O>o-CH3O ≫ o-HO, o-Cl.
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3.
The propenylimines that are formed during isomerization are found in the cis and trans configurations. Based on the NMR spectral data, the amount of the cis isomer in the mixture is 60–70%.
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4.
On the basis of the spectral data it was postulated that the 2-azadiene system in the alkylidene- and benzylidenepropenylamines, which is formed as a result of the catalytic transformations, exists in the syn-cis and syn-trans configurations.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2038–2045, September, 1975.
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Dol'skaya, Y.S., Chizhov, O.S. & Golovina, N.I. Unsaturated amines Communication 14. Stereochemistry of isomeric transformations of N-allylimines. Russ Chem Bull 24, 1919–1925 (1975). https://doi.org/10.1007/BF00930165
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DOI: https://doi.org/10.1007/BF00930165