An unexpected 1,2-hydride shift in phosphoric acid-promoted cyclodimerization of styrene oxides under solvent-free conditions. A synthetic route towards 2,4-disubstituted 1,3-dioxolanes

Ofentse Mazimba, Runner R. Majinda, Ishmael B. Masesane

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

A 1,2-hydride shift in the phosphoric acid-promoted cyclodimerization of styrene oxide and its chloro derivatives under solvent-free conditions leading to 2,4-disubstituted 1,3-dioxolanes is described. Methoxy substituents on the aromatic ring of the styrene oxide prevent the 1,2-hydride shift reaction leading to substituted 1,4-dioxanes. A possible mechanism for the formation of the 1,3-dioxolanes is proposed.
Original languageEnglish
Pages (from-to)5927-5929
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number43
DOIs
Publication statusPublished - 2009

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