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Scope and limitations of the Peterson olefination reaction as a route to vinylidene phosphanes

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.

Publication metadata

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


DOI: 10.1002/ejoc.200300683


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