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New examples of base-promoted acetal formation in the reactions of aryl salicylate and salicylate-type esters 1 to 3 with aldehydes are reported.

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1996 substitution reactions substitution reactions O 0040 -056The Reactions of Aryl Acrylates under Baylis-Hillman Conditions.-Aryl acrylates (I) react with aromatic aldehydes in a DABCO-mediated coupling reaction to yield α-substituted acrylates. However, application of aliphatic aldehydes results in formation of cyclic acetals (VII) as exclusive or side product (in the case of (IV)→ (VIII)) depending on the acrylate aryl moiety and the amount of aldehyde used. -(PERLMUTTER, P.; PUNIANI, E.; WESTMAN, G.; Tetrahedron