Formation of 1,1-dimethylallyl derivatives by reaction of 3,3-dimethylallyl halides with copper(ii) chelates of acetylacetone and methyl acetoacetate

J.A. Miller, Rona Black, J. Larkin, D.C. Nonhebel, H.C.S. Wood, Scrimego.C.M

Research output: Contribution to journal › Article

12 Citations (Scopus)

Abstract

Alkylation of the copper(II) chelates of acetylacetone and methyl acetoacetate by 3,3-dimethylallyl halides yields both 3,3-dimethylallyl and 1,1-dimethylallyl products. Formation of 1,1-dimethylallyl derivatives of these -polyketide analogues appears to be the results of a direct C-alkylation, and is a significant characteristic of the copper chelate reactions, which has not been observed previously with other alkylation reactions of -diketones or -keto-esters.
Original languageEnglish
Pages (from-to)603-606
Number of pages3
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number6
DOIs
Publication statusPublished - 1973

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Alkylation
Copper
Derivatives
Polyketides
Esters
methyl acetoacetate
acetylacetone

Keywords

  • 1
  • 1-dimethylallyl
  • 3
  • 3-dimethylallyl halides
  • copper(ii) chelates
  • cetylacetone
  • methyl acetoacetate

Cite this

Miller, J.A. ; Black, Rona ; Larkin, J. ; Nonhebel, D.C. ; Wood, H.C.S. ; Scrimego.C.M. / Formation of 1,1-dimethylallyl derivatives by reaction of 3,3-dimethylallyl halides with copper(ii) chelates of acetylacetone and methyl acetoacetate. In: Journal of the Chemical Society, Perkin Transactions 1. 1973 ; No. 6. pp. 603-606.
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title = "Formation of 1,1-dimethylallyl derivatives by reaction of 3,3-dimethylallyl halides with copper(ii) chelates of acetylacetone and methyl acetoacetate",
abstract = "Alkylation of the copper(II) chelates of acetylacetone and methyl acetoacetate by 3,3-dimethylallyl halides yields both 3,3-dimethylallyl and 1,1-dimethylallyl products. Formation of 1,1-dimethylallyl derivatives of these -polyketide analogues appears to be the results of a direct C-alkylation, and is a significant characteristic of the copper chelate reactions, which has not been observed previously with other alkylation reactions of -diketones or -keto-esters.",
keywords = "1, 1-dimethylallyl, 3, 3-dimethylallyl halides, copper(ii) chelates, cetylacetone, methyl acetoacetate",
author = "J.A. Miller and Rona Black and J. Larkin and D.C. Nonhebel and H.C.S. Wood and Scrimego.C.M",
year = "1973",
doi = "10.1039/P19730000603",
language = "English",
pages = "603--606",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
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Miller, JA, Black, R, Larkin, J, Nonhebel, DC, Wood, HCS & Scrimego.C.M 1973, 'Formation of 1,1-dimethylallyl derivatives by reaction of 3,3-dimethylallyl halides with copper(ii) chelates of acetylacetone and methyl acetoacetate', Journal of the Chemical Society, Perkin Transactions 1, no. 6, pp. 603-606. https://doi.org/10.1039/P19730000603

Formation of 1,1-dimethylallyl derivatives by reaction of 3,3-dimethylallyl halides with copper(ii) chelates of acetylacetone and methyl acetoacetate. / Miller, J.A.; Black, Rona; Larkin, J.; Nonhebel, D.C.; Wood, H.C.S.; Scrimego.C.M.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 6, 1973, p. 603-606.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Formation of 1,1-dimethylallyl derivatives by reaction of 3,3-dimethylallyl halides with copper(ii) chelates of acetylacetone and methyl acetoacetate

AU - Miller, J.A.

AU - Black, Rona

AU - Larkin, J.

AU - Nonhebel, D.C.

AU - Wood, H.C.S.

AU - Scrimego.C.M

PY - 1973

Y1 - 1973

N2 - Alkylation of the copper(II) chelates of acetylacetone and methyl acetoacetate by 3,3-dimethylallyl halides yields both 3,3-dimethylallyl and 1,1-dimethylallyl products. Formation of 1,1-dimethylallyl derivatives of these -polyketide analogues appears to be the results of a direct C-alkylation, and is a significant characteristic of the copper chelate reactions, which has not been observed previously with other alkylation reactions of -diketones or -keto-esters.

AB - Alkylation of the copper(II) chelates of acetylacetone and methyl acetoacetate by 3,3-dimethylallyl halides yields both 3,3-dimethylallyl and 1,1-dimethylallyl products. Formation of 1,1-dimethylallyl derivatives of these -polyketide analogues appears to be the results of a direct C-alkylation, and is a significant characteristic of the copper chelate reactions, which has not been observed previously with other alkylation reactions of -diketones or -keto-esters.

KW - 1

KW - 1-dimethylallyl

KW - 3

KW - 3-dimethylallyl halides

KW - copper(ii) chelates

KW - cetylacetone

KW - methyl acetoacetate

U2 - 10.1039/P19730000603

DO - 10.1039/P19730000603

M3 - Article

SP - 603

EP - 606

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

IS - 6

ER -

Miller JA, Black R, Larkin J, Nonhebel DC, Wood HCS, Scrimego.C.M. Formation of 1,1-dimethylallyl derivatives by reaction of 3,3-dimethylallyl halides with copper(ii) chelates of acetylacetone and methyl acetoacetate. Journal of the Chemical Society, Perkin Transactions 1. 1973;(6):603-606. https://doi.org/10.1039/P19730000603

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