Linear and branched phospha[n]triangulanes

J.C. Slootweg; F.J.J. De Kanter; M. Schakel; A.W. Ehlers; S.I. Koshushkov; A. de Meijere; M. Lutz; A.L. Spek; K. Lammertsma

doi:10.1002/chem.200500538

Linear and branched phospha[n]triangulanes

J.C. Slootweg, F.J.J. De Kanter, M. Schakel, A.W. Ehlers, S.I. Koshushkov, A. de Meijere, M. Lutz, A.L. Spek, K. Lammertsma

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

Novel, highly stable, linear and branched mono- and diphospha[n]triangulanes were synthesized in high yields by the CuCl-catalyzed phosphinidene addition to spirocyclopropanated methylenecyclopropanes and bicyclopropylidenes. The effect of spirofusion on the electronic properties of these esthetically attractive phosphacycles is apparent from X-ray single crystal structure analyses, which reveals a tightening of the phosphirane ring on additional spirocyclopropanation, and from the NMR features that show deshielded chemical shifts for the ring-phosphorus and -carbon atoms. Steric factors play a role in the addition reaction when the substrate alkene carries a second sphere of spirocyclopropane rings and causes the formation of 2-phosphabicyclo[3.2.0]heptenes in small amounts. These by-products most probably result from addition of the [PhP(Cl)W(CO)

Original language	English
Journal	Chemistry: A European Journal
DOIs	https://doi.org/10.1002/chem.200500538
Publication status	Published - 2005

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10.1002/chem.200500538

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CCDC 269697: Experimental Crystal Structure Determination
Slootweg, J. C. (Contributor), De Kanter, F. J. J. (Contributor), Schakel, M. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), Kozhushkov, S. I. (Contributor), De Meijere, A. (Contributor) & Lammertsma, K. (Contributor), Unknown Publisher, 1 Jan 2006
DOI: 10.5517/cc91mxv, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc91mxv&sid=DataCite
Dataset / Software: Dataset
CCDC 269698: Experimental Crystal Structure Determination
Slootweg, J. C. (Contributor), De Kanter, F. J. J. (Contributor), Schakel, M. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), Kozhushkov, S. I. (Contributor), De Meijere, A. (Contributor) & Lammertsma, K. (Contributor), Unknown Publisher, 1 Jan 2006
DOI: 10.5517/cc91myw, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc91myw&sid=DataCite
Dataset / Software: Dataset
CCDC 269695: Experimental Crystal Structure Determination
Slootweg, J. C. (Contributor), De Kanter, F. J. J. (Contributor), Schakel, M. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), Kozhushkov, S. I. (Contributor), De Meijere, A. (Contributor) & Lammertsma, K. (Contributor), Unknown Publisher, 1 Jan 2006
DOI: 10.5517/cc91mvs, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc91mvs&sid=DataCite
Dataset / Software: Dataset

Cite this

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title = "Linear and branched phospha[n]triangulanes",

abstract = "Novel, highly stable, linear and branched mono- and diphospha[n]triangulanes were synthesized in high yields by the CuCl-catalyzed phosphinidene addition to spirocyclopropanated methylenecyclopropanes and bicyclopropylidenes. The effect of spirofusion on the electronic properties of these esthetically attractive phosphacycles is apparent from X-ray single crystal structure analyses, which reveals a tightening of the phosphirane ring on additional spirocyclopropanation, and from the NMR features that show deshielded chemical shifts for the ring-phosphorus and -carbon atoms. Steric factors play a role in the addition reaction when the substrate alkene carries a second sphere of spirocyclopropane rings and causes the formation of 2-phosphabicyclo[3.2.0]heptenes in small amounts. These by-products most probably result from addition of the [PhP(Cl)W(CO)",

author = "J.C. Slootweg and {De Kanter}, F.J.J. and M. Schakel and A.W. Ehlers and S.I. Koshushkov and {de Meijere}, A. and M. Lutz and A.L. Spek and K. Lammertsma",

year = "2005",

doi = "10.1002/chem.200500538",

language = "English",

journal = "Chemistry: A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

}

TY - JOUR

T1 - Linear and branched phospha[n]triangulanes

AU - Slootweg, J.C.

AU - De Kanter, F.J.J.

AU - Schakel, M.

AU - Ehlers, A.W.

AU - Koshushkov, S.I.

AU - de Meijere, A.

AU - Lutz, M.

AU - Spek, A.L.

AU - Lammertsma, K.

PY - 2005

Y1 - 2005

N2 - Novel, highly stable, linear and branched mono- and diphospha[n]triangulanes were synthesized in high yields by the CuCl-catalyzed phosphinidene addition to spirocyclopropanated methylenecyclopropanes and bicyclopropylidenes. The effect of spirofusion on the electronic properties of these esthetically attractive phosphacycles is apparent from X-ray single crystal structure analyses, which reveals a tightening of the phosphirane ring on additional spirocyclopropanation, and from the NMR features that show deshielded chemical shifts for the ring-phosphorus and -carbon atoms. Steric factors play a role in the addition reaction when the substrate alkene carries a second sphere of spirocyclopropane rings and causes the formation of 2-phosphabicyclo[3.2.0]heptenes in small amounts. These by-products most probably result from addition of the [PhP(Cl)W(CO)

AB - Novel, highly stable, linear and branched mono- and diphospha[n]triangulanes were synthesized in high yields by the CuCl-catalyzed phosphinidene addition to spirocyclopropanated methylenecyclopropanes and bicyclopropylidenes. The effect of spirofusion on the electronic properties of these esthetically attractive phosphacycles is apparent from X-ray single crystal structure analyses, which reveals a tightening of the phosphirane ring on additional spirocyclopropanation, and from the NMR features that show deshielded chemical shifts for the ring-phosphorus and -carbon atoms. Steric factors play a role in the addition reaction when the substrate alkene carries a second sphere of spirocyclopropane rings and causes the formation of 2-phosphabicyclo[3.2.0]heptenes in small amounts. These by-products most probably result from addition of the [PhP(Cl)W(CO)

U2 - 10.1002/chem.200500538

DO - 10.1002/chem.200500538

M3 - Article

SN - 0947-6539

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

ER -

Linear and branched phospha[n]triangulanes

Abstract

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Datasets

CCDC 269697: Experimental Crystal Structure Determination

CCDC 269698: Experimental Crystal Structure Determination

CCDC 269695: Experimental Crystal Structure Determination

Cite this