Vierundzwanzigste Abhandlung. Ueber die Hydrierung geschlossener Ringe

Stohmann, F.; Kleber, Cl.

doi:10.1002/prac.18910430151

Cited by 6 publications

(7 citation statements)

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“…[21]), nucleophilic displacement of CI3 by ethoxide ion (Eq. [25]) is necessary to balance the electron count, and the net effect of Eq. [22]) to methyl iodide (Eq.…”

Section: [9]mentioning

confidence: 99%

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Syntheses with Electrogenerated Halogens: Part II . Oxidation of Malonate Esters

White

1977

J. Electrochem. Soc.

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The indirect electrochemical oxidation of malonate esters (I) to ethane-1,1,2,2-tetracarboxylate esters (II) has been investigated in greater detail than previously reported. With acetonitrile or an alcohol as the solvent, ethenetetracarboxylate (III), propane-l,l,2,2,3,3-hexacarboxylate (IV), and ethane-1,1,2-tricarboxylate (V) esters were also formed. If the conversion of (I) was limited to 70%, by-product formation was low and 98% yields of (II) were obtained. In acetonitrile, current efficiency was comparable with the chemical yield, but with alcoholic solvents it was lower (70-80%) due to competing indirect oxidation of the alcohol to the corresponding alkyl formate (VI). The similar coupling of monosubstituted malonate esters (VII; giving VIII) shows a marked steric effect similar to that observed in some cyanoethylation reactions, suggesting that the coupling occurs via a nucleophilic displacement reaction. The steric effect rationalizes the absence of tetrameric and higher products. The similar cyclization of some bismalonate esters (IX; giving X) is also reported.

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“…[21]), nucleophilic displacement of CI3 by ethoxide ion (Eq. [25]) is necessary to balance the electron count, and the net effect of Eq. [22]) to methyl iodide (Eq.…”

Section: [9]mentioning

confidence: 99%

“…[22]), reduction of the iodoform also formed in (Eq. [20]- [25] is summarized by Eq. [23]), and reaction of methyl iodide in a Williamson ether synthesis-type reaction (Eq.…”

Section: [9]mentioning

confidence: 99%

Syntheses with Electrogenerated Halogens: Part II . Oxidation of Malonate Esters

White

1977

J. Electrochem. Soc.

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“…The old data on the heats of combustion of styrene yield values which differ from the foregoing value by the following amounts, in percent: Stohmann, et a1. [17], -0.15 ±0.20; Auwers, et a1. [18], +0.05±0.10; Lemoult [19], +1.1±0.6; Moureu and Andre [20], -0.13±0.20; Landrieu, et a1.…”

Section: Styrenementioning

confidence: 99%

“…The existing values for the heats of combustion and formation of styrene are based on old measurements of the heat of combustion [17,18,19,20,21,22). New data on the heat of combustion of styrene obtained in this laboratory [16) yield a more reliable value for its heat of formation from the elements, as well as for its heat of combustion.…”

Section: Introductionmentioning

confidence: 99%