SCHEDULED MAINTENANCE
Thiophene-2-carbaldehyde adds to aromatic and aliphatic aldehydes with the mediation of samarium diiodide and hexamethylphosphoramide. These hydroxyalkylations occur at the 5-position of thiophene-2-carbaldehyde. The self- and cross-coupling reactions of thiophene-3-carbaldehyde occur at the 2-position. S-Alkylation of the reaction intermediates gives substituted γ-lactols.
S. Yang and J. Fang, J. Chem. Soc., Perkin Trans. 1, 1995, 2669 DOI: 10.1039/P19950002669
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