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A new method for synthesis of n-(3-acyloxypropyl)-substituted six- to thirteen-membered alkan-n-olides

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Abstract

A new method for the synthesis of n-(3-acyloxypropyl)-substituted six- to thirteen-membered alkan-n-olides was developed. The method is based on the H2SO4-catalyzed reactions of oxabicycloalkenes, obtained from 2-(3-acetoxypropyl)cycloalkanes, with H2O2 and formic or acetic acid. The method includes the subsequent transformations of oxabicycloalkenes into bicyclic hydroperoxides, peroxy ethers, and, at the final stage, into target lactones formed in 56—71% yields. These transformations are carried as a one-pot reaction.

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Authors and Affiliations

  1. Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    Yu. N. Ogibin, A. V. Kutkin, A. O. Terent"ev & G. I. Nikishin

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  1. Yu. N. Ogibin
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  2. A. V. Kutkin
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  3. A. O. Terent"ev
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  4. G. I. Nikishin
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Ogibin, Y.N., Kutkin, A.V., Terent"ev, A.O. et al. A new method for synthesis of n-(3-acyloxypropyl)-substituted six- to thirteen-membered alkan-n-olides. Russian Chemical Bulletin 51, 1806–1811 (2002). https://doi.org/10.1023/A:1021336031371

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