Issue 2, 1989
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Dienediolates from unsaturated carboxylic acids. Reaction with para-substituted benzaldehydes. Electronic effects on regioselectivity

Margarita Parra,   Ramon Mestres,   Domitila Aparicio,   Nieves Durana  and  Gloria Rubiales  

Abstract

Regioselectivity α/γ ratios for addition of the lithium dienediolate of crotonic acid to para-substituted benzaldehydes are subject to small electronic effects when reactions are carried out at low temperature, but strong influence by substituents is observed on heating for 1 h at 60 °C. A linear correlation is then found between regiochemical ratios and σp parameters. Stereoselectivity RR/RS ratios (33 : 66 to 43 : 57) for α-adducts obtained in the cold do not depend on the substituents.

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Article information

DOI
https://doi.org/10.1039/P19890000327
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1989, 327-332

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Dienediolates from unsaturated carboxylic acids. Reaction with para-substituted benzaldehydes. Electronic effects on regioselectivity

M. Parra, R. Mestres, D. Aparicio, N. Durana and G. Rubiales, J. Chem. Soc., Perkin Trans. 1, 1989, 327 DOI: 10.1039/P19890000327

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