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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 13-14
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Original Articles

A Facile Synthesis of Ethyl 3-Aryl-2,2-dimethyl-cyclopropanecarboxylates, Intermediates for Pyrethroid Acaricides

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Pages 2515-2521 | Received 15 Mar 1989, Published online: 24 Oct 2006

References

  • Ozawa , K. , Ishii , S. , Hirata , K. and Hirose , M. 1982 . Phenylcyclopropanecarboxylic acid esters as new pyrethroid acaricides and insecticides. Abstracts of the 5th International Congress of Pesticide Chemistry, Kyoto (Japan), Paper 1a-7.
  • Arlt , D. , Jautelat , M. and Lantzsch , R. 1981 . Angew. Chem. Int. Ed. Engl. , 20 : 703
  • Happer , O. A. R. and Steenson , B. C. 1980 . Synthesis , : 806
  • Milot , J. M. , Boullet , F. T. and Foucad , A. 1987 . Synthesis , : 364 For similar reaction of 2-nitropropane with alkylidene cyanoacetates and malonates, 7, see:
  • Krief , A. , Hevesi , L. , Chaboteaux , G. , Mathyl , P. , Servin , M. and Devos , M. J. 1985 . J. Chem. Soc. Chem. Commun. , : 1693
  • Ono , N. , Yanai , T. , Hamamoto , I. , Kamimura , A. and Kaji , A. 1985 . J. Org. Chem. , 50 : 2807
  • Babbler , J. H. and Spina , K. P. 1985 . Tetrahedron Lett. , 26 : 1923
  • See references 4 (a) and 4 (c).
  • Trost , B. M. , Arndt , H. C. , Strege , P. E. and Verhoeven , T. R. 1976 . Tetrahedron Lett. , : 3477
  • Patel , D. J. , Howden , M. E. H. and Roberts , J. D. 1963 . J. Am. Chem. Soc. , 85 : 3218 This ratio was determined from the relative intensities of the cyclopropyl CH3's as well as the vicinal cyclopropyl hydrogens by 1H NMR analysis. The stereochemical assignments were based on the known greater coupling constants (9–10 Hz) for cis vicinal cyclopropyl hydrogens than for the trans isomer (6–7 Hz) and the greater chemical shift difference for the geminal CH3's of the trans isomer. Our values were in agreement with those reported by
  • Genet , J. P. , Devis , A. and Charbonnier , F. 1986 . Bull. Soc. Chim. Fr. , : 793
  • Ashley , W. C. and Shriner , R. L. 1932 . J. Am. Chem. Soc. , 54 : 4410 however, we obtained much higher yields using solvent PEG-400 as given by Sukata, K., Bull. Chem. Soc. Jpn., 1984, 57, 613.

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