Anlagerung von Diäthylphosphit an eine Doppelbindung

Schwarzenbach, G.; Ruckstuhl, P.; Zurc, J.

doi:10.1002/hlca.19510340209

Cited by 7 publications

(3 citation statements)

References 4 publications

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“…A considerable number of organophosphorus compounds have been prepared by the addition of dialkyl phosphonates to ethylenic double bonds conjugated with certain "activating" groups. These groups include the dialkylphosphono (141,193,202,206,207,217,222), oxo (35,36,140,192,194,198,203,204,212), cyano (35,36,199,203,205,213), carboalkoxy (35,36,195,197,199,200,203,205,213), carbamyl (199), and carboxy (199) groups. This method was first described by Pudovik but was discovered independently in a number of other laboratories.…”

Section: Miscellaneous Methodsmentioning

confidence: 99%

The Preparation And Properties Of Phosphonic Acids

Freedman¹,

Doak²

1957

Chem. Rev.

237

145

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Section: Miscellaneous Methodsmentioning

confidence: 99%

The Preparation And Properties Of Phosphonic Acids

Freedman¹,

Doak²

1957

Chem. Rev.

237

145

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“…Since CH3OH is the only volatile product produced under these conditions, the decomposition is probably best represented by eq 2, xGeHaOCH3 --+ (GeH2j2 + xCH30H (2) where (GeH2). However, over a period of several hours i t decomposes slowly in the liquid phase, even at temperatures below -23".…”

Section: Resultsmentioning

confidence: 99%

Preparation and properties of germyl methyl ether and germylmethyl methyl ether

Gibbon¹,

Wang²,

Dyke³

1967

Inorg. Chem.

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GERMYL METHYL ETHER AND GERMYLMETHYL METHYL ETHER 1989 metal-ammonia solutions, we propose the mechanism 21 --23 e . 4-GeHI -3 GeH8 -t. H 2BIn this mechanism,5 one would expect the rate of formation of amide ion (which catalyzes the Ge(NH)z-producing reaction), relative to the rate of reaction 4, to increase with increasing metal concentration. The mechanism thus explains the excess hydrogen formed at high metal concentrations. The same mechanism is applicable to the analogous reactions of silane and stannane if we assume that, on going from SiH4 to GeH4 to SnH4, the protonic acidity increases and the susceptibility to displacement of hydride ion by amide ion decreases.Acknowledgments.-This work was sponsored by the U. S. Atomic Energy Commission and the National Science Foundation.(24) The rate-determining step in the formation of Ge(NHda is probably reaction 8, because the germanium would become more positive as the number of amino groups increases (inductive effect) and, consequently, more susceptible to nucleophilic attack by amide.26 From the data in Table 11, we calculate ks/ks = 0.18. (25) F. Rijkens and G. J. M. Van Der Kerk, "Investigations in the Field ofThe synthesis, characterization, and some properties of GeH30CH3 and GeH3CH20CH8 are described. The donor properties of the compounds have been investigated by an infrared hydrogen-bonding study. Germyl methyl ether acts as a stronger Lewis base than (C&)zo, and GeHaCHzOCHa acts as a weaker Lewis base than CH3CHzOCH3, with methanol as reference acid. The results are compared with data for the corresponding silicon compounds and discussed in terms of electronegativity and rr-bonding considerations.

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“…When diethyl phosphite is heated with butanol or a higher alcohol, ethyl alcohol is eliminated, leaving a mixed ester (188). The reaction of a dialkyl sodiophosphite with allyl chloride may give a dialkyl allyl phosphonate (188) or addition to th'e double bond may take place leading to a tetraalkyltrimethylene diphosphonate (196). Yellow phosphorus unites with an alkyl disulfide to form a trialkyl trithiophosphite (809).…”

Section: Phosphorous and Phosphoric Estersmentioning

confidence: 99%