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

Research output: Contribution to journalJournal articleResearchpeer-review

Celia Clarke, David J Fox, Daniel Sejer Pedersen, Stuart Warren

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.
Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Volume7
Issue number7
Pages (from-to)1329-1336
ISSN1477-0520
DOIs
Publication statusPublished - 2009

Bibliographical note

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

ID: 13087361