Rapid one-pot synthesis of cycloheptatriene-phosphonium derivatives

Samantha M. Kruse; Stephanie K. Hurst

doi:10.1016/j.tetlet.2015.06.097

Rapid one-pot synthesis of cycloheptatriene-phosphonium derivatives

Samantha M. Kruse, Stephanie K. Hurst

Chemistry and Biochemistry

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

8 Scopus citations

Abstract

The direct combination reaction of tropylium tetrafluoroborate with a range of mono- and bi-dentate phosphines in chlorinated solvents leads to the formation of a series of cycloheptatriene-phosphonium derivatives in excellent yields. Multi-nuclear NMR and single-crystal X-ray diffraction studies confirm the addition of the tropylium ligand to the phosphorous centre to form cycloheptatriene derivatives.

Original language	English (US)
Pages (from-to)	6319-6322
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	46
DOIs	https://doi.org/10.1016/j.tetlet.2015.06.097
State	Published - Nov 18 2015

Keywords

Cycloheptatriene
Dppe
Dppf
Dppp
Phosphonium
Tropylium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.06.097

Cite this

@article{f20a71ed72a7492eb4e3075c7a378e8d,

title = "Rapid one-pot synthesis of cycloheptatriene-phosphonium derivatives",

abstract = "The direct combination reaction of tropylium tetrafluoroborate with a range of mono- and bi-dentate phosphines in chlorinated solvents leads to the formation of a series of cycloheptatriene-phosphonium derivatives in excellent yields. Multi-nuclear NMR and single-crystal X-ray diffraction studies confirm the addition of the tropylium ligand to the phosphorous centre to form cycloheptatriene derivatives.",

keywords = "Cycloheptatriene, Dppe, Dppf, Dppp, Phosphonium, Tropylium",

author = "Kruse, {Samantha M.} and Hurst, {Stephanie K.}",

note = "Funding Information: We wish to thank Northern Arizona University and the College of Engineering, Forestry and Natural Sciences. Crystallographic data for 2 – 4 were collected at Beamline 11.3.1 at the Advanced Light Source (ALS), Lawrence Berkeley National Laboratory. The ALS is supported by the U.S. Department of Energy, Office of Energy Sciences , under Contract DE-AC02-05CH11231 . We thank the Research Corporation for Science Advancement for their support though the Cottrell College Science Award (ID 10600 ). We also thank and the American Chemical Society Petroleum Research Fund (ACS-PRF Grant # 51546-UR3 ). We wish to extend our thanks to Dr. Gary Nichol of the University of Edinburgh for fruitful discussions, and to the 2013 American Crystallographic Association Summer Course in Chemical Crystallography. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

month = nov,

day = "18",

doi = "10.1016/j.tetlet.2015.06.097",

language = "English (US)",

volume = "56",

pages = "6319--6322",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "46",

}

TY - JOUR

T1 - Rapid one-pot synthesis of cycloheptatriene-phosphonium derivatives

AU - Kruse, Samantha M.

AU - Hurst, Stephanie K.

N1 - Funding Information: We wish to thank Northern Arizona University and the College of Engineering, Forestry and Natural Sciences. Crystallographic data for 2 – 4 were collected at Beamline 11.3.1 at the Advanced Light Source (ALS), Lawrence Berkeley National Laboratory. The ALS is supported by the U.S. Department of Energy, Office of Energy Sciences , under Contract DE-AC02-05CH11231 . We thank the Research Corporation for Science Advancement for their support though the Cottrell College Science Award (ID 10600 ). We also thank and the American Chemical Society Petroleum Research Fund (ACS-PRF Grant # 51546-UR3 ). We wish to extend our thanks to Dr. Gary Nichol of the University of Edinburgh for fruitful discussions, and to the 2013 American Crystallographic Association Summer Course in Chemical Crystallography. Publisher Copyright: © 2015 Elsevier Ltd.

PY - 2015/11/18

Y1 - 2015/11/18

N2 - The direct combination reaction of tropylium tetrafluoroborate with a range of mono- and bi-dentate phosphines in chlorinated solvents leads to the formation of a series of cycloheptatriene-phosphonium derivatives in excellent yields. Multi-nuclear NMR and single-crystal X-ray diffraction studies confirm the addition of the tropylium ligand to the phosphorous centre to form cycloheptatriene derivatives.

AB - The direct combination reaction of tropylium tetrafluoroborate with a range of mono- and bi-dentate phosphines in chlorinated solvents leads to the formation of a series of cycloheptatriene-phosphonium derivatives in excellent yields. Multi-nuclear NMR and single-crystal X-ray diffraction studies confirm the addition of the tropylium ligand to the phosphorous centre to form cycloheptatriene derivatives.

KW - Cycloheptatriene

KW - Dppe

KW - Dppf

KW - Dppp

KW - Phosphonium

KW - Tropylium

UR - http://www.scopus.com/inward/record.url?scp=84946102661&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84946102661&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.06.097

DO - 10.1016/j.tetlet.2015.06.097

M3 - Article

AN - SCOPUS:84946102661

VL - 56

SP - 6319

EP - 6322

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 46

ER -

Rapid one-pot synthesis of cycloheptatriene-phosphonium derivatives

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 1502997: Experimental Crystal Structure Determination

CCDC 1502996: Experimental Crystal Structure Determination

CCDC 1502995: Experimental Crystal Structure Determination

Cite this

Rapid one-pot synthesis of cycloheptatriene-phosphonium derivatives

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1502997: Experimental Crystal Structure Determination

CCDC 1502996: Experimental Crystal Structure Determination

CCDC 1502995: Experimental Crystal Structure Determination

Cite this