The importance of the Lewis base in lithium mediated metallation and bond cleavage reaction of allyl amines and allyl phosphines

V. L. Blair, M. A. Stevens, C. D. Thompson

Research output: Contribution to journalArticleOtherpeer-review

2 Citations (Scopus)

Abstract

Metallation of two analogous N- and P-allyl molecules Ph2NCH2CHCH21 and Ph2PCH2CHCH22 with nBuLi have shown contrasting reactivities based on the choice of Lewis donor. With 1 metallation of the alpha carbon atom was achieved regardless of the Lewis donor used while in comparison metallation of 2 showed an unexpected donor denticity dependence with P-C bond clevage induced with the tri-dentate PMDETA. Complementary DFT and solution studies rationalise this outcome.

Original languageEnglish
Pages (from-to)8111-8114
Number of pages4
JournalChemical Communications
Volume52
Issue number52
DOIs
Publication statusPublished - 2016

Cite this

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abstract = "Metallation of two analogous N- and P-allyl molecules Ph2NCH2CHCH21 and Ph2PCH2CHCH22 with nBuLi have shown contrasting reactivities based on the choice of Lewis donor. With 1 metallation of the alpha carbon atom was achieved regardless of the Lewis donor used while in comparison metallation of 2 showed an unexpected donor denticity dependence with P-C bond clevage induced with the tri-dentate PMDETA. Complementary DFT and solution studies rationalise this outcome.",
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The importance of the Lewis base in lithium mediated metallation and bond cleavage reaction of allyl amines and allyl phosphines. / Blair, V. L.; Stevens, M. A.; Thompson, C. D.

In: Chemical Communications, Vol. 52, No. 52, 2016, p. 8111-8114.

Research output: Contribution to journalArticleOtherpeer-review

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AB - Metallation of two analogous N- and P-allyl molecules Ph2NCH2CHCH21 and Ph2PCH2CHCH22 with nBuLi have shown contrasting reactivities based on the choice of Lewis donor. With 1 metallation of the alpha carbon atom was achieved regardless of the Lewis donor used while in comparison metallation of 2 showed an unexpected donor denticity dependence with P-C bond clevage induced with the tri-dentate PMDETA. Complementary DFT and solution studies rationalise this outcome.

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JF - Chemical Communications

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