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

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Author list: Mazimba O, Majinda RR, Masesane IB

Publisher: Elsevier

Place: OXFORD

Publication year: 2009

Journal: Tetrahedron Letters (0040-4039)

Journal acronym: TETRAHEDRON LETT

Volume number: 50

Issue number: 43

Start page: 5927

End page: 5929

Number of pages: 3

ISSN: 0040-4039

Languages: English-Great Britain (EN-GB)

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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. (C) 2009 Elsevier Ltd. All rights reserved.

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