P. Ooms, R. Bos, J. Scheeren
1977
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0
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1
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
Treatment of ethyl 2,2,3,3-tetraalkoxy-1-cyanocyclobutanecarboxylates (7), obtained by heating tetraalkoxyethenes with ethyl 2-cyano-2-alkenoates at 100°, with a dilute methanolic solution of sodium hydroxide at 50° leads to hydrolysis of the ester function. On prolonged heating at higher temperatures the resulting products 8 decarboxylate, yielding 2,2,3>3-tetraalkoxycyclobutanecarbonitriles 9. Under these conditions the nitrile group is also partly hydrolysed to a carboxylic acid function. Depending on the pH, acidification of 8 yields either rearranged, six-membered ring compounds, viz. 4,4,5,5-tetraalkoxy-2-cyano-δ-valerolactones 12, or acyclic acetals of α-keto esters 13.