Synthese des symmetrischen Homo‐tetrahydro‐isochinolins

Braun, Julius v.; Reich, H.

doi:10.1002/cber.19250581211

Cited by 5 publications

(1 citation statement)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The methiodide was formed with methyl iodide in ethanol and was recrystallized from ethanol, m.p. 230-231°, reported (12) m.p. 227°.…”

Section: IImentioning

confidence: 99%

o-Phenylenediacetimide and other Compounds Related to 3, 1H-Benzazepine

Halford¹,

Weissmann²

1952

J. Org. Chem.

View full text Add to dashboard Cite

o-Phenylenediacetamide has been cyclized pyrolytically to o-phenylenediacetimide. The yield at 295" was 57% on a 190-mg. scale and 53% on a 2-g. scale, while less satisfactory yields were obtained at higher or lower temperatures. About 10% of the diamide was recovered. Attempts to improve the yield by conducting the reaction under dilution in boiling phenyl ether (ammonia evolution 87%, imide recovered 12%) and in boiling phenol (ammonia evolution slow) were not successful.This apparent contradiction of the dilution principle has a fairly satisfactory explanation. If it is assumed that only amide linkages are formed and that the system is approaching equilibrium, there should be in a single phase a distribution of cyclic polymers whose mean molecular weight would decrease with increasing temperature or with dilution. The distribution, because of these two factors, should be about the same in the pyrolysis (higher temperature) and in the phenyl ether experiment (dilution). The pyrolytic reaction produces the better result because the product, along with a smaller quantity of the diamide, sublimes out of the sphere of reaction. It is possible, but less probable, that the

show abstract

“…The methiodide was formed with methyl iodide in ethanol and was recrystallized from ethanol, m.p. 230-231°, reported (12) m.p. 227°.…”

Section: IImentioning

confidence: 99%