30238-19-8Relevant academic research and scientific papers
Convenient and practical alkynylation of heteronucleophiles with copper acetylides
Theunissen, Cedric,Lecomte, Morgan,Jouvin, Kevin,Laouiti, Anouar,Guissart, Celine,Heimburger, Jeremy,Loire, Estelle,Evano, Gwilherm
, p. 1157 - 1166 (2014/05/20)
Copper acetylides, readily available reagents which are characterized by their lack of reactivity, can be simply activated by oxidation with oxygen in the presence of simple nitrogen ligands such as TMEDA or imidazole derivatives. Upon activation, these nucleophilic species undergo a formal umpolung and can transfer their alkyne subunit to a wide range of heteronucleophiles, including amides, oxazolidinones, imines, and dialkyl phosphites. This alkynylation, which provides one of the most practical entry to useful building blocks such as ynamides, ynimines, and alkynylphosphonates, proceeds under especially mild conditions and can be easily performed on a multigram scale. Georg Thieme Verlag Stuttgart, New York.
Transformation of alkynyl sulfones into alkynylphosphonates with trialkyl phosphites
Yatsumonji, Yasutaka,Ogata, Akitoshi,Tsubouchi, Akira,Takeda, Takeshi
, p. 2265 - 2267 (2008/09/18)
1-Alkynylphosphonates were obtained in good to high yields by simple heating of 1-alkynyl sulfones with trialkyl phosphites.
Synthesis, Structure, and Reactivity of Metal Derivatives of Diethyl Ester of 1-Propynephosphonic Acid (1-DEPP)
Kirilov, Marko,Petrov, Galin,Sidjimov, Atanass
, p. 1351 - 1358 (2007/10/02)
Metallation of diethyl ester of 1-propynephosphonic acid (1-DEPP) is achieved by treatment with alkaline amides, calcium amid and calcium in liquid ammonia, with isopropylmagnesium chloride in ether or via metal exchange from the potassium derivative of 1-DEPP with copper(II) and cobalt(II) chloride resp.On the basis of IR- and 1H-NMR-spectra the calcium derivative appears as a mixture of an allene and its isomeric acetylene.The IR-spectrum of the lithium derivative is consistent with an analogous phenomenon while an acetylene structure is attributed only to the cobalt and copper derivatives.The alkylation of the potassium derivative with alkyl halides and the hydroxyalkylation with benzaldehyde occur with low yield at the γ-position of the parent compound. - Key words: Allene-acetylene isomerization; Metal derivatives; Phosphonic acid derivatives
