The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes. / Clarke, Celia; Fox, David J; Pedersen, Daniel Sejer; Warren, Stuart.

In: Organic & Biomolecular Chemistry, Vol. 7, No. 7, 2009, p. 1329-1336.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Clarke, C, Fox, DJ, Pedersen, DS & Warren, S 2009, 'The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes', Organic & Biomolecular Chemistry, vol. 7, no. 7, pp. 1329-1336. https://doi.org/10.1039/b817436a

APA

Clarke, C., Fox, D. J., Pedersen, D. S., & Warren, S. (2009). The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes. Organic & Biomolecular Chemistry, 7(7), 1329-1336. https://doi.org/10.1039/b817436a

Vancouver

Clarke C, Fox DJ, Pedersen DS, Warren S. The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes. Organic & Biomolecular Chemistry. 2009;7(7):1329-1336. https://doi.org/10.1039/b817436a

Author

Clarke, Celia ; Fox, David J ; Pedersen, Daniel Sejer ; Warren, Stuart. / The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes. In: Organic & Biomolecular Chemistry. 2009 ; Vol. 7, No. 7. pp. 1329-1336.

Bibtex

@article{e77bb7c06d3611de8bc9000ea68e967b,
title = "The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes",
abstract = "Phosphine oxides are lithiated much faster than phosphine sulfides and phosphine boranes. Phosphine sulfides are in turn lithiated much more readily than phosphine boranes. It was possible to trap a phosphine sulfide THF in one case which upon treatment with t-BuOK gave cyclopropane, showing that phosphine sulfides readily undergo both phosphinoyl transfer and cyclopropane ring closure just like their phosphine oxide counterparts. The obtained data show that phosphine oxides are easily lithiated and undergo phosphoryl transfer much more readily and faster than phosphine sulfides and phosphine boranes. The observations suggest that it would be possible to perform reactions involving phosphine oxides in the presence of phosphine boranes or phosphine sulfides, potentially allowing regioselective alkylation of phosphine oxides in the presence of phosphine boranes or phosphine sulfides.",
keywords = "Former Faculty of Pharmaceutical Sciences",
author = "Celia Clarke and Fox, {David J} and Pedersen, {Daniel Sejer} and Stuart Warren",
note = "Keywords: Boranes; Computer Simulation; Crystallography, X-Ray; Cyclopropanes; Lithium; Models, Chemical; Models, Molecular; Molecular Structure; Organometallic Compounds; Oxides; Phosphines; Stereoisomerism; Sulfides",
year = "2009",
doi = "10.1039/b817436a",
language = "English",
volume = "7",
pages = "1329--1336",
journal = "Organic & Biomolecular Chemistry",
issn = "1470-4358",
publisher = "Royal Society of Chemistry",
number = "7",

}

RIS

TY - JOUR

T1 - The lithiation and acyl transfer reactions of phosphine oxides, sulfides and boranes in the synthesis of cyclopropanes

AU - Clarke, Celia

AU - Fox, David J

AU - Pedersen, Daniel Sejer

AU - Warren, Stuart

N1 - Keywords: Boranes; Computer Simulation; Crystallography, X-Ray; Cyclopropanes; Lithium; Models, Chemical; Models, Molecular; Molecular Structure; Organometallic Compounds; Oxides; Phosphines; Stereoisomerism; Sulfides

PY - 2009

Y1 - 2009

N2 - Phosphine oxides are lithiated much faster than phosphine sulfides and phosphine boranes. Phosphine sulfides are in turn lithiated much more readily than phosphine boranes. It was possible to trap a phosphine sulfide THF in one case which upon treatment with t-BuOK gave cyclopropane, showing that phosphine sulfides readily undergo both phosphinoyl transfer and cyclopropane ring closure just like their phosphine oxide counterparts. The obtained data show that phosphine oxides are easily lithiated and undergo phosphoryl transfer much more readily and faster than phosphine sulfides and phosphine boranes. The observations suggest that it would be possible to perform reactions involving phosphine oxides in the presence of phosphine boranes or phosphine sulfides, potentially allowing regioselective alkylation of phosphine oxides in the presence of phosphine boranes or phosphine sulfides.

AB - Phosphine oxides are lithiated much faster than phosphine sulfides and phosphine boranes. Phosphine sulfides are in turn lithiated much more readily than phosphine boranes. It was possible to trap a phosphine sulfide THF in one case which upon treatment with t-BuOK gave cyclopropane, showing that phosphine sulfides readily undergo both phosphinoyl transfer and cyclopropane ring closure just like their phosphine oxide counterparts. The obtained data show that phosphine oxides are easily lithiated and undergo phosphoryl transfer much more readily and faster than phosphine sulfides and phosphine boranes. The observations suggest that it would be possible to perform reactions involving phosphine oxides in the presence of phosphine boranes or phosphine sulfides, potentially allowing regioselective alkylation of phosphine oxides in the presence of phosphine boranes or phosphine sulfides.

KW - Former Faculty of Pharmaceutical Sciences

U2 - 10.1039/b817436a

DO - 10.1039/b817436a

M3 - Journal article

C2 - 19300817

VL - 7

SP - 1329

EP - 1336

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1470-4358

IS - 7

ER -

ID: 13087361