DOI: 10.1002/recl.19740931204. Insertion of phenyl isocyanide into ethanol catalysed simultaneously by copper(I) and base

Insertion of phenyl isocyanide into ethanol catalysed simultaneously by copper(I) and base

10.1002/recl.19740931204

Crossref journal-article

Wiley

Recueil des Travaux Chimiques des Pays-Bas (311)

Abstract

AbstractThe insertion of phenyl isocyanide into ethanol under the influence of base and Cu(PhNC)4BF4 is investigated mechanistically. In pre‐equilibria the BF4⊖ anion is exchanged for ⊖OC2H5. By intramolecular nucleophilic attack of ⊖OC2H5 on coordinated isocyanide an [(ethoxy)‐(phenylimino)methyl]copper intermediate is formed. The substituent effect supports this conclusion. In a rapid reaction with ethanol the intermediate decomposes and the insertion product, ethyl N‐phenylformimidate, is formed. It reacts slowly to give N,N′‐diphenylformamidine, which is precipitated at the end of the reaction as a copper complex.

Bibliography

Knol, D., van Os, C. P. A., & Drenth, W. (1974). Insertion of phenyl isocyanide into ethanol catalysed simultaneously by copper(I) and base. Recueil Des Travaux Chimiques Des Pays-Bas, 93(12), 314â316. Portico.

Authors 3

D. Knol (first)
C. P. A. van Os (additional)
W. Drenth (additional)

References 16 Referenced 11

aT.Saegusa Y.Ito S.KobayashiandK.Hirota Tetrahedron Lett.521(1967). (10.1016/S0040-4039(00)90541-0)
bT.Saegusa Y.Ito S.Kobayashi N.TakedaandK.Hirota Tetrahedron Lett.1273(1967). (10.1016/S0040-4039(00)90683-X)
10.1139/v69-196
10.1080/00945717108057275
10.1021/ic50112a028
10.1016/S0022-328X(00)95178-7
R. W.Stephany unpublished results.
10.1021/ja01329a006
{'key': 'e_1_2_1_6_2', 'volume-title': 'The principles of electrochemistry', 'author': 'MacInnes D. A.', 'year': '1961'} / The principles of electrochemistry by MacInnes D. A. (1961)
E. F.CaldinandG.Long J. Chem. Soc.3737(1954). (10.1039/JR9540003737)
{'key': 'e_1_2_1_8_2', 'volume-title': 'Isonitrile Chemistry', 'author': 'Saegusa T.', 'year': '1971'} / Isonitrile Chemistry by Saegusa T. (1971)
10.1016/S0022-328X(00)93034-1
10.1021/ja00750a019
N.Koga G.KogaandJ.‐P.Anselme Tetrahedron Lett.3309(1970). (10.1016/S0040-4039(01)98460-6)
W. P.WeberandG. W.Gokel Tetrahedron Lett.1637(1972). (10.1016/S0040-4039(01)84707-9)
10.1002/ange.19710830405

Dates

Type	When
Created	14 years, 11 months ago (Sept. 13, 2010, 11:53 p.m.)
Deposited	1 year, 10 months ago (Oct. 17, 2023, 8:14 p.m.)
Indexed	1 year, 9 months ago (Nov. 5, 2023, 5:37 p.m.)
Issued	51 years, 8 months ago (Jan. 1, 1974)
Published	51 years, 8 months ago (Jan. 1, 1974)
Published Online	15 years ago (Sept. 2, 2010)
Published Print	51 years, 8 months ago (Jan. 1, 1974)

Funders 0

None

BibTeX

@article{Knol_1974, title={Insertion of phenyl isocyanide into ethanol catalysed simultaneously by copper(I) and base}, volume={93}, ISSN={0165-0513}, url={http://dx.doi.org/10.1002/recl.19740931204}, DOI={10.1002/recl.19740931204}, number={12}, journal={Recueil des Travaux Chimiques des Pays-Bas}, publisher={Wiley}, author={Knol, D. and van Os, C. P. A. and Drenth, W.}, year={1974}, month=jan, pages={314–316} }

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