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Lookup NU author(s): Dr Keith Izod, Emeritus Professor William McFarlane, Brent Tyson
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The Peterson olefination reaction has been investigated as a route to novel P-substituted alkenes. The reaction between [(nPr2P) 2(Me3Si)C]Li and paraformaldehyde cleanly gives the symmetrical vinylidene phosphane (nPr2P)2C=CH2 (4) in good to excellent yields. In contrast, reactions between [(R 2P)(Me3Si)2C]Li (R = Me, nPr) and paraformaldehyde yield complex mixtures of products which do not contain the expected vinylidene species. However, the unsymmetrical vinylidene phosphanes [nPr2P(BH3)](Me3Si)C=CH2 (6), (Ph2P)(iPr2P)C=CH2 (7), [nPr 2P(S)](Me3Si)C=CH2 (10), [Ph 2P(S)][iPr2P(S)]C=CH2 (11) and [Ph 2P(S)][Me2P(S)]C=CH2 (12) are readily accessible by the Peterson olefination reaction {compound 7 is obtained by deprotection of the corresponding borane adduct [Ph2P(BH 3)][iPr2P(BH3)]C=CH2 with pyrrolidine}. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Author(s): Izod K, McFarlane W, Tyson BV
Publication type: Article
Publication status: Published
Journal: European Journal of Organic Chemistry
Year: 2004
Issue: 5
Pages: 1043-1048
ISSN (print): 1434-193X
ISSN (electronic): 1099-0690
Publisher: Wiley - VCH Verlag GmbH & Co. KGaA
URL: http://dx.doi.org/10.1002/ejoc.200300683
DOI: 10.1002/ejoc.200300683
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