Efficient synthesis of cyclic β-oxophosphoranes by microwave-assisted reaction of cyclic phosphine oxides and dialkyl acetylenedicarboxylates

G. Keglevich, Eszter Dudás, M. Sipos, Dóra Lengyel, K. Ludányi

Research output: Article

27 Citations (Scopus)

Abstract

The inverse Wittig-type reaction of a series of 2,4,6-trialkylphenyl cyclic phosphine oxides 3, 5, 7, 9, 11, 13, 15, 18 and 20 and dialkyl acetylenedicarboxylate giving β-oxophosphoranes 4, 6, 8, 10, 12, 14, 16, 19 and 21, respectively, can be accomplished in a convenient way under microwave conditions. At 150 °C, the MW-assisted reaction is more efficient and becomes 50-fold faster as compared to the thermal transformation. A further advantage is that the 2,5-dihydrophosphole moiety of the 2,4,6- triisopropylphenyl derivative 3 does not undergo double-bond rearrangement and that the 2,4,6-trimethylphenyl substrates 11 and 13, otherwise inactive in the reaction under discussion, could also be converted to β-oxophosphoranes 12 and 14. A series of new products 4Bb, 12, 14, 16b, 19 and 21 have been made available.

Original languageEnglish
Pages (from-to)1365-1369
Number of pages5
JournalSynthesis
Issue number8
DOIs
Publication statusPublished - ápr. 19 2006

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phosphine
Oxides
Microwaves
Derivatives
Substrates
Hot Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Efficient synthesis of cyclic β-oxophosphoranes by microwave-assisted reaction of cyclic phosphine oxides and dialkyl acetylenedicarboxylates",
abstract = "The inverse Wittig-type reaction of a series of 2,4,6-trialkylphenyl cyclic phosphine oxides 3, 5, 7, 9, 11, 13, 15, 18 and 20 and dialkyl acetylenedicarboxylate giving β-oxophosphoranes 4, 6, 8, 10, 12, 14, 16, 19 and 21, respectively, can be accomplished in a convenient way under microwave conditions. At 150 °C, the MW-assisted reaction is more efficient and becomes 50-fold faster as compared to the thermal transformation. A further advantage is that the 2,5-dihydrophosphole moiety of the 2,4,6- triisopropylphenyl derivative 3 does not undergo double-bond rearrangement and that the 2,4,6-trimethylphenyl substrates 11 and 13, otherwise inactive in the reaction under discussion, could also be converted to β-oxophosphoranes 12 and 14. A series of new products 4Bb, 12, 14, 16b, 19 and 21 have been made available.",
keywords = "Alkyne derivatives, Cyclic phosphine oxides, Inverse-Wittig reactions, Microwave synthesis, Phosphoranes, Ylides",
author = "G. Keglevich and Eszter Dud{\'a}s and M. Sipos and D{\'o}ra Lengyel and K. Lud{\'a}nyi",
year = "2006",
month = "4",
day = "19",
doi = "10.1055/s-2006-926395",
language = "English",
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journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
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TY - JOUR

T1 - Efficient synthesis of cyclic β-oxophosphoranes by microwave-assisted reaction of cyclic phosphine oxides and dialkyl acetylenedicarboxylates

AU - Keglevich, G.

AU - Dudás, Eszter

AU - Sipos, M.

AU - Lengyel, Dóra

AU - Ludányi, K.

PY - 2006/4/19

Y1 - 2006/4/19

N2 - The inverse Wittig-type reaction of a series of 2,4,6-trialkylphenyl cyclic phosphine oxides 3, 5, 7, 9, 11, 13, 15, 18 and 20 and dialkyl acetylenedicarboxylate giving β-oxophosphoranes 4, 6, 8, 10, 12, 14, 16, 19 and 21, respectively, can be accomplished in a convenient way under microwave conditions. At 150 °C, the MW-assisted reaction is more efficient and becomes 50-fold faster as compared to the thermal transformation. A further advantage is that the 2,5-dihydrophosphole moiety of the 2,4,6- triisopropylphenyl derivative 3 does not undergo double-bond rearrangement and that the 2,4,6-trimethylphenyl substrates 11 and 13, otherwise inactive in the reaction under discussion, could also be converted to β-oxophosphoranes 12 and 14. A series of new products 4Bb, 12, 14, 16b, 19 and 21 have been made available.

AB - The inverse Wittig-type reaction of a series of 2,4,6-trialkylphenyl cyclic phosphine oxides 3, 5, 7, 9, 11, 13, 15, 18 and 20 and dialkyl acetylenedicarboxylate giving β-oxophosphoranes 4, 6, 8, 10, 12, 14, 16, 19 and 21, respectively, can be accomplished in a convenient way under microwave conditions. At 150 °C, the MW-assisted reaction is more efficient and becomes 50-fold faster as compared to the thermal transformation. A further advantage is that the 2,5-dihydrophosphole moiety of the 2,4,6- triisopropylphenyl derivative 3 does not undergo double-bond rearrangement and that the 2,4,6-trimethylphenyl substrates 11 and 13, otherwise inactive in the reaction under discussion, could also be converted to β-oxophosphoranes 12 and 14. A series of new products 4Bb, 12, 14, 16b, 19 and 21 have been made available.

KW - Alkyne derivatives

KW - Cyclic phosphine oxides

KW - Inverse-Wittig reactions

KW - Microwave synthesis

KW - Phosphoranes

KW - Ylides

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U2 - 10.1055/s-2006-926395

DO - 10.1055/s-2006-926395

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EP - 1369

JO - Synthesis

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