Transition‐Metal‐Catalysed Reactions of Diazoesters: Synthesis of Chrysanthemic and Permethric Acid Esters by Cyclopropanation of Conjugated Dienes

Demonceau, Albert; Noels, Alfred; Anciaux, A. J.; Hubert, André J.; Teyssié, Philippe

doi:10.1002/bscb.19840931104

Article (Scientific journals)

Transition‐Metal‐Catalysed Reactions of Diazoesters: Synthesis of Chrysanthemic and Permethric Acid Esters by Cyclopropanation of Conjugated Dienes

Demonceau, Albert; Noels, Alfred; Anciaux, A. J. et al.

1984 • In Bulletin des Sociétés Chimiques Belges, 93 (11), p. 949-952

Peer reviewed

Permalink
https://hdl.handle.net/2268/237693

DOI
10.1002/bscb.19840931104

Files (1)Send to Details Statistics Bibliography Similar publications

Files

Full Text

TEYSSIE_01.pdf

Publisher postprint (383.2 kB)

Download

All documents in ORBi are protected by a user license.

Send to

RIS BibTex APA Chicago Permalink X Linkedin

Details

Abstract :

[en] Pyrethroid precursors (permethric and chrysanthemic acid esters) are efficiently synthesized by rhodium(II)‐catalysed cyclopropanation of the properly substituted conjugated diene. Reaction selectivities depend on both the catalyst counter‐ion and the diazoester alkoxy‐group (carbene precursor) and are attributed to non‐bonded interactions. Copyright © 1984 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim

Disciplines :

Chemistry

Author, co-author :

Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Noels, Alfred ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)

Anciaux, A. J.; Laboratory of Macromolecular Chemistry and Organic Catalysis, Laboratory of Organic Synthesis and Catalysis, University of Liège, Sart-Tilman, B-4000, Belgium

Hubert, André J.

Teyssié, Philippe ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)

Language :

English

Title :

Transition‐Metal‐Catalysed Reactions of Diazoesters: Synthesis of Chrysanthemic and Permethric Acid Esters by Cyclopropanation of Conjugated Dienes

Publication date :

1984

Journal title :

Bulletin des Sociétés Chimiques Belges

ISSN :

0037-9646

Publisher :

John Wiley & Sons, United Kingdom

Volume :

Issue :

Pages :

949-952

Peer reviewed :

Peer reviewed

Available on ORBi :

since 29 June 2019

Statistics

Number of views

54 (2 by ULiège)

Number of downloads

91 (1 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

Elliott M., Farnham A.W., Janes N.F., Needham P.H., Pulman D.A., Stevenson J.H. Nature 1973, 246:169.
Bader A. Aldrichimica Acta 1976, 9:49.
Gent J.P., Piau F., Ficini J., Tetrahedron Lett.; 1980, 3183.
Gent J.P., Piau F. (1981) Palladium-catalyzed reactions: stereoselective synthesis of substituted cyclopropanes related to chrysanthemic acid. A simple route to cis-chrysanthemonitrile. The Journal of Organic Chemistry 46:2414.
Lehmkuhi H., Mehler K., Liebigs Ann. Chem.; 1982, 2244.
Lantzsch R., Synthesis; 1982, 955.
Mitra R.B., Muljiani Z., Deshmukh A.R.A.S. Synth. Commun. 1982, 12:1063.
Ho T.‐L., Din Z.U. Synth. Commun. 1982, 12:257.
Ho T.‐L., Liu S.‐H. Synth. Commun. 1982, 12:995.
Ho T.‐L. Synth. Commun. 1983, 13:761.
Babler J.H., Haack R.A. Synth. Commun. 1983, 13:905.
d'Angelo J., Revial G., Tetrahedron Lett.; 1983, 2103.
Schneider M., Engel N., Boensmann H. (1984) Enzymatic Syntheses of Chiral Building Blocks from Racemates: Preparation of(1R,3R)-Chrysanthemic, -Permethrinic and -Caronic Acids from Racemic, Diastereomeric Mixtures. Angewandte Chemie International Edition in English 23:64.
Farkaŝ J., Kour̂m P., Ŝorm F. (1959) Relation between chemical structure and insecticidal activity in pyrethroid compounds. I. An analogue of chrysanthemic acid containing chlorine in the side chain. Collection of Czechoslovak Chemical Communications 24:2230.
Holland D., Laidler D.A., Milner D.J. J. Mol. Cat. 1981, 11:119.
Csiz L., 3rd International Symposium on Homogeneous Catalysis, August 30‐September 3, 1982, Milano, Abstract Fr 13, p. 183. However, some chiral copper catalysts have been used successfully.; .
Aratani T., Yoneyoshi Y., Nagase T., Tetrahedron Lett.; 1975, 1707.
Aratani T., Yoneyoshi Y., Nagase T., Tetrahedron Lett.; 1977, 2599.
Aratani T., Yoneyoshi Y., Nagase T., Tetrahedron Lett.; 1982, 685.
Anciaux A.J., Hubert A.J., Noels A.F., Petiniot N., Teyssi P. J. Org. Chem. 1980, 45:695.
Anciaux A.J., Demonceau A., Noels A.F., Warin R., Hubert A.J., Teyssi P. Tetrahedron 1983, 39:2169.
Holland D., Milner D.J., J. Chem. Research (S); 1979, 317.
Holland D., Milner D.J., J. Chem. Research (S); 1979, 3734.
.