A study on the optical resolution of 1-isopropyl-3-methyl-3-phospholene 1-oxide and its use in the synthesis of borane and platinum complexes

Péter Bagi, Kinga Juhász, István Timári, Katalin E. Kövér, Dávid Mester, Mihály Kállay, Miklós Kubinyi, Tibor Szilvási, Péter Pongrácz, László Kollár, Konstantin Karaghiosoff, Mátyás Czugler, László Drahos, Elemér Fogassy, György Keglevich

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10 Citations (Scopus)

Abstract

A 1-isopropyl-3-phospholene 1-oxide was prepared and the two enantiomers were isolated from the racemate by resolution using optically active TADDOL derivatives or the acidic Ca2+ salts of (-)-O,O-diaroyl-(2R,3R)-tartaric acids. The single crystal X-ray structure of the 1-isopropyl-3-phospholene oxide - spiro-TADDOL 1:2 associate revealed the mode of binding between the host and guest molecules. The role of the interactions between the three molecules was supported not only by the contact data, but also force field and semiempirical calculations. Beside X-ray analysis, the absolute configuration of the P-stereogenic center was also determined on the basis of CD spectroscopy and high level quantum chemical calculations. The racemic and optically active 1-isopropyl-3-phospholenes obtained after deoxygenation were converted to the corresponding borane complexes and Pt(II) complexes. Stereostructure of the latter species was evaluated by high level quantum chemical calculations and the Pt complexes were tested as catalysts in the hydroformylation of styrene.

Original languageEnglish
Pages (from-to)140-152
Number of pages13
JournalJournal of Organometallic Chemistry
Volume797
DOIs
Publication statusPublished - Nov 15 2015

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Keywords

  • 3-Phospholene oxide
  • Hydroformylation
  • Optical resolution
  • Pt-complexes
  • Theoretical calculations
  • X-ray structure

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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