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Transformation of carboxylic acid esters into 2-substituted allyl halides through tertiary cyclopropyl sulfonates. Application in the synthesis of (±)-ipsenol and (±)-ipsdienol, components of Ips typographus spark beetle pheromone

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Abstract

Cyclopropanation of the ester group in ethyl 3-chloropropanoate and subsequent cleavage of the three-membered carbocycle in intermediate 1-(2-chloroethyl)cyclopropyl methanesulfonate gave 2-bromomethyl-4-chlorobut-1-ene, and the latter was used as key intermediate in the synthesis of racemic ipsenol and ipsdienol which are components of Ips typographus L. European spruce spark beetle pheromone.

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Authors and Affiliations

  1. Belarussian State University, pr. Skoriny 4, Minsk, 220050, Belarus

    E. A. Matyushenkov & O. G. Kulinkovich

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  1. E. A. Matyushenkov
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  2. O. G. Kulinkovich
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Original Russian Text © E.A. Matyushenkov, O.G. Kulinkovich, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 4, pp. 509–513.

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Matyushenkov, E.A., Kulinkovich, O.G. Transformation of carboxylic acid esters into 2-substituted allyl halides through tertiary cyclopropyl sulfonates. Application in the synthesis of (±)-ipsenol and (±)-ipsdienol, components of Ips typographus spark beetle pheromone. Russ J Org Chem 42, 491–495 (2006). https://doi.org/10.1134/S1070428006040038

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  • DOI: https://doi.org/10.1134/S1070428006040038

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