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Cyclodimerization of the Stevens Rearrangement Products from 4-Alkoxy-2-butynyl(alkoxycarbonylmethyl)dimethyl-ammonium Salts into Cyclohexene Derivatives

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Abstract

4-Alkoxy-2-butynyl(alkoxycarbonyl)dimethylammonium salts undergo 3,2-Stevens rearrangement by the action of the corresponding sodium alkoxides. Hydrolysis of the rearrangement products with dilute hydrochloric acid gives 3-alkoxy-2-oxo-3-pentenoic acid esters which are converted into 3-methylene-2-oxo-4-pentenoates via 1,4-elimination of alcohol. [2 + 4]-Cyclodimerization of 3-methylene-2-oxo-4-pentenoates leads to 1,4-bis(alkoxalyl)-4-vinylcyclohexenes.

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Authors
  1. A. V. Babakhanyan
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  2. V. S. Ovsepyan
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  3. G. A. Panosyan
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  4. S. T. Kocharyan
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Babakhanyan, A.V., Ovsepyan, V.S., Panosyan, G.A. et al. Cyclodimerization of the Stevens Rearrangement Products from 4-Alkoxy-2-butynyl(alkoxycarbonylmethyl)dimethyl-ammonium Salts into Cyclohexene Derivatives. Russian Journal of Organic Chemistry 40, 936–939 (2004). https://doi.org/10.1023/B:RUJO.0000045180.02568.65

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  • DOI: https://doi.org/10.1023/B:RUJO.0000045180.02568.65

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