Dynamic NMR study of the oxaphosphetane complexation with lithium during the Wittig reaction

Dynamic NMR spectroscopy at very low temperatures (148–182 K) reveal the dynamic behavior of the (2‐tri(3‐furyl)‐3‐methyl‐4‐cyclopropenyl‐oxaphosphetane) generated during a Wittig reaction between tri(3‐furyl)ethylphosphonium iodine and cyclopropylaldehyde. The possibility of formation of different...

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Published inInternational journal of quantum chemistry Vol. 108; no. 6; pp. 1052 - 1058
Main Authors Pascariu, Aurelia, Mracec, Mircea, Berger, Stefan
Format Journal Article
LanguageEnglish
Published Hoboken Wiley Subscription Services, Inc., A Wiley Company 2008
Subjects
dynamic NMR spectroscopy
lithium complexation
oxaphosphetanes
quantum mechanical calculations
Wittig reactions
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Summary:Dynamic NMR spectroscopy at very low temperatures (148–182 K) reveal the dynamic behavior of the (2‐tri(3‐furyl)‐3‐methyl‐4‐cyclopropenyl‐oxaphosphetane) generated during a Wittig reaction between tri(3‐furyl)ethylphosphonium iodine and cyclopropylaldehyde. The possibility of formation of different adducts between Li+ ions and oxaphosphetane or betainic intermediates was checked calculating the formation enthalpies using the MNDO, AM1, and PM3 semiempirical MO methods. The observed species are interpreted as oxaphosphetane complexes with lithium ions present in solution. Quantum mechanical calculations confirm the spectroscopic results. © 2008 Wiley Periodicals, Inc. Int J Quantum Chem, 2008
Bibliography:istex:86713CEDF66B1B5D408FA0B58F752BDE1E5311CB
ArticleID:QUA21602
National Councilor for Research and High Education (CNCSIS) - No. nr.776/2005/Agrement 27658/2005/GR177/2006/1973/2006
Fifth Framework Programme (Marie Curie Fellowship) - No. HPTM 2000-00183
ark:/67375/WNG-NLBN1RGZ-T
ISSN:0020-7608
1097-461X
DOI:10.1002/qua.21602