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