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

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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.
Original languageEnglish
Pages (from-to)5927-5929
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number43
DOIs
Publication statusPublished - 2009

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styrene oxide
Hydrides
Derivatives
phosphoric acid
formal glycol

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title = "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",
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.",
author = "Ofentse Mazimba and Majinda, {Runner R.} and Masesane, {Ishmael B.}",
year = "2009",
doi = "10.1016/j.tetlet.2009.08.044",
language = "English",
volume = "50",
pages = "5927--5929",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
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TY - JOUR

T1 - 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

AU - Mazimba, Ofentse

AU - Majinda, Runner R.

AU - Masesane, Ishmael B.

PY - 2009

Y1 - 2009

N2 - 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.

AB - 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.

U2 - 10.1016/j.tetlet.2009.08.044

DO - 10.1016/j.tetlet.2009.08.044

M3 - Article

VL - 50

SP - 5927

EP - 5929

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 43

ER -