Toggle Main Menu Toggle Search

Open Access padlockePrints

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

Downloads

Full text for this publication is not currently held within this repository. Alternative links are provided below where available.


Abstract

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

URL: http://dx.doi.org/10.1002/ejoc.200300683

DOI: 10.1002/ejoc.200300683


Altmetrics

Altmetrics provided by Altmetric


Share