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New possible ionic structures in Wittig reaction: Analysis of stability and rotation barriers by semiempirical PM3 method
Author(s) -
Mracec Maria,
Pascariu Aurelia,
Berger Stefan,
Mracec Mircea
Publication year - 2007
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.21298
Subject(s) - wittig reaction , chemistry , ionic bonding , phosphine oxide , benzaldehyde , phosphine , computational chemistry , ionic liquid , organic chemistry , catalysis , ion
For the Wittig reaction between butylidentriphenylphosphorane and benzaldehyde studied previously using NMR spectroscopy, three ionic intermediates have been proposed in order to explain the “stereochemical drift” (different ratio in oxaphosphetane stereoisomers compared with the ratio of the final Z / E olefins). In this paper, the PM3 semiempirical MO method was applied on the proposed ionic intermediates. Two of the ionic intermediates could lead to a shift of the reaction towards the final products, olefins and phosphine oxide, while the third intermediate could be implicated in a retro‐Wittig reaction. © 2007 Wiley Periodicals, Inc. Int J Quantum Chem, 2007