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

doi:10.1016/j.tetlet.2009.08.044

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

Chemical & Forensic Sciences

Research output: Contribution to journal › Article › peer-review

11 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 language	English
Pages (from-to)	5927-5929
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2009.08.044
Publication status	Published - 2009

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10.1016/j.tetlet.2009.08.044

http://www.sciencedirect.com/science/article/pii/S0040403909015895

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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 Ltd",

number = "43",

}

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. / Mazimba, Ofentse; Majinda, Runner R.; Masesane, Ishmael B.
In: Tetrahedron Letters, Vol. 50, No. 43, 2009, p. 5927-5929.

Research output: Contribution to journal › Article › peer-review

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

SN - 0040-4039

VL - 50

SP - 5927

EP - 5929

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

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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