Acetylene-substituted phosphane oxides: Building blocks for macrocycles

Sander G.A. Van Assema; G. Bas De Jong; Andreas W. Ehlers; Frans J.J. De Kanter; Marius Schakel; Anthony L. Spek; Martin Lutz; Koop Lammertsma

doi:10.1002/ejoc.200600877

Acetylene-substituted phosphane oxides: Building blocks for macrocycles

Sander G.A. Van Assema, G. Bas De Jong, Andreas W. Ehlers, Frans J.J. De Kanter, Marius Schakel, Anthony L. Spek, Martin Lutz, Koop Lammertsma

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

Phosphorus-based macrocycles with acetylenic scaffolds have been built from acetylene-substituted phosphane oxides that were formed from diisopropylphosphoramidic dibromide (3) and an acetylenic Grignard reagent. The four-and six-edged macrocycles 15 and 16, in which the iPr₂NP(O) units are connected through 1,3-butadiyne rods, were obtained from the monosilylated derivative of iPr₂NP(O)(C₂H)₂ (7) by multiple acetylene coupling reactions under oxidative Hay conditions. Reaction of iPr₂NP(O)(Br)₂ (3) with lithiated 1,2-diethynylbenzene gave a mixture of cis and trans monocyclic bis(phosphane oxide) 18. An X-ray crystal structure determination of the trans isomer shows the ring structure to adopt a puckered form.

Original language	English
Pages (from-to)	2405-2412
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	15
DOIs	https://doi.org/10.1002/ejoc.200600877
Publication status	Published - 2007
Externally published	Yes

Keywords

Alkynes
Cross-coupling
Macrocycles
Phosphanes
Phosphorus heterocycles

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.200600877

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title = "Acetylene-substituted phosphane oxides: Building blocks for macrocycles",

abstract = "Phosphorus-based macrocycles with acetylenic scaffolds have been built from acetylene-substituted phosphane oxides that were formed from diisopropylphosphoramidic dibromide (3) and an acetylenic Grignard reagent. The four-and six-edged macrocycles 15 and 16, in which the iPr2NP(O) units are connected through 1,3-butadiyne rods, were obtained from the monosilylated derivative of iPr2NP(O)(C2H)2 (7) by multiple acetylene coupling reactions under oxidative Hay conditions. Reaction of iPr2NP(O)(Br)2 (3) with lithiated 1,2-diethynylbenzene gave a mixture of cis and trans monocyclic bis(phosphane oxide) 18. An X-ray crystal structure determination of the trans isomer shows the ring structure to adopt a puckered form.",

keywords = "Alkynes, Cross-coupling, Macrocycles, Phosphanes, Phosphorus heterocycles",

author = "{Van Assema}, {Sander G.A.} and {De Jong}, {G. Bas} and Ehlers, {Andreas W.} and {De Kanter}, {Frans J.J.} and Marius Schakel and Spek, {Anthony L.} and Martin Lutz and Koop Lammertsma",

year = "2007",

doi = "10.1002/ejoc.200600877",

language = "English",

pages = "2405--2412",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "15",

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TY - JOUR

T1 - Acetylene-substituted phosphane oxides

T2 - Building blocks for macrocycles

AU - Van Assema, Sander G.A.

AU - De Jong, G. Bas

AU - Ehlers, Andreas W.

AU - De Kanter, Frans J.J.

AU - Schakel, Marius

AU - Spek, Anthony L.

AU - Lutz, Martin

AU - Lammertsma, Koop

PY - 2007

Y1 - 2007

N2 - Phosphorus-based macrocycles with acetylenic scaffolds have been built from acetylene-substituted phosphane oxides that were formed from diisopropylphosphoramidic dibromide (3) and an acetylenic Grignard reagent. The four-and six-edged macrocycles 15 and 16, in which the iPr2NP(O) units are connected through 1,3-butadiyne rods, were obtained from the monosilylated derivative of iPr2NP(O)(C2H)2 (7) by multiple acetylene coupling reactions under oxidative Hay conditions. Reaction of iPr2NP(O)(Br)2 (3) with lithiated 1,2-diethynylbenzene gave a mixture of cis and trans monocyclic bis(phosphane oxide) 18. An X-ray crystal structure determination of the trans isomer shows the ring structure to adopt a puckered form.

AB - Phosphorus-based macrocycles with acetylenic scaffolds have been built from acetylene-substituted phosphane oxides that were formed from diisopropylphosphoramidic dibromide (3) and an acetylenic Grignard reagent. The four-and six-edged macrocycles 15 and 16, in which the iPr2NP(O) units are connected through 1,3-butadiyne rods, were obtained from the monosilylated derivative of iPr2NP(O)(C2H)2 (7) by multiple acetylene coupling reactions under oxidative Hay conditions. Reaction of iPr2NP(O)(Br)2 (3) with lithiated 1,2-diethynylbenzene gave a mixture of cis and trans monocyclic bis(phosphane oxide) 18. An X-ray crystal structure determination of the trans isomer shows the ring structure to adopt a puckered form.

KW - Alkynes

KW - Cross-coupling

KW - Macrocycles

KW - Phosphanes

KW - Phosphorus heterocycles

UR - http://www.scopus.com/inward/record.url?scp=34250645881&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200600877

DO - 10.1002/ejoc.200600877

M3 - Article

AN - SCOPUS:34250645881

SN - 1434-193X

SP - 2405

EP - 2412

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 15

ER -

Acetylene-substituted phosphane oxides: Building blocks for macrocycles

Abstract

Keywords

ASJC Scopus subject areas

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