ChemInform Abstract: Unexpected Heteroatom‐Assisted C‐4 Alkylation of a 1,3‐Dioxolane.

Abstract

Unexpected Heteroatom-Assisted C-4 Alkylation of a 1,3-Dioxolane.-The 2-pyridylthiomethyldioxolane (I) is cleaved upon treatment with the Grignard compounds (IIa) -(IIc) to form the 3-(2-pyridylthio) propanols (III). Experiments with other related dioxolanes show that both the pyridyl and the thiomethylene moiety are necessary for this reaction. -(MAROT, C.; PHILIPP, C.; ROLLIN, P.; Tetrahedron Lett. 33 (1992) 32, 4575-4578; Lab. Chim. Bioorg. Analyt., Ass. CNRS, Univ., 45067 Orleans, Fr.; EN)