Vinylphosphine: synthesis by flash vacuum pyrolysis, stability, and spectroscopic properties

Lasne, Marie‐Claire; Ripoll, Jean‐Louis; Thuillier, André

doi:10.1039/c39860001428

Cited by 19 publications

(15 citation statements)

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“…From this study we find that, as for ethenylphosphine (5),5 the free rotation of the phosphino moiety in allenylphosphines plays an important role in interpreting the PE spectra. The favored rotamer is found to have the phosphorus lone pair interacting with the trC2-c3 orbital, the presence of the orthogonal orbital of the allenic skeleton raising the energy of the gauche conformations.…”

Section: Discussionmentioning

confidence: 71%

Application of photoelectron spectroscopy to molecular properties. 46. Gas-phase structure and stability of alkynylphosphines and allenylphosphines: photoelectronic study

Lacombe¹,

Wang²,

Pfister‐Guillouzo³

et al. 1992

Inorg. Chem.

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Compounds bearing a heterosubstituted double or triple bond such as ethenol, ethynol, ethenamine, or ethynamine have been the subject of extensive theoretical investigations.2 However, due to the high instability of these compounds, the experimental characterizations of the unsubstituted parent molecules have been performed either in matrix3 or in the gas phase by mass or photoelectron spectroscopy4 (PES). To our knowledge similar studies on phosphorus compounds are limited to ethenylphos-phinesS5 We report here our results on the gas-phase structure and reactivity of alkynyl-and allenylphosphines monitored by photoelectron spectroscopy. PE Spectra of Akyayland AllenylpbosphinesAlkynyl-and allenylphosphines are cleanly produced by mild reduction with dichloroalane (AlHCh) in tetraglyme of the corresponding alkynyl-or allenylphosphonates, respectivelye6 The reductions are performed on a vacuum line directly connected, via a cryogenic trap, to the PES inlet. In this way the volatile phosphines are continuously distilled,from the reaction mixture to the cryogenic trap (100 K). After subsequent heating of the trap to the suitable temperature, the analysis of the phosphines is completed by recording the PE spectra of the gaseous flow. This gaseous flow may also be trapped on a cold finger fitted to an NMR tube, bypassing the PES inlet. The NMR spectra of (1) Application of Photoelectron Spectroscopy to Molecular Properties. 46. Part 45: Chuburu, F.; Lacombc, S.; Wster-Guillouzo, G.; Ben Cheik, A,; Chuche, J.; Pommelet, J. C.

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Section: Discussionmentioning

confidence: 71%

Application of photoelectron spectroscopy to molecular properties. 46. Gas-phase structure and stability of alkynylphosphines and allenylphosphines: photoelectronic study

Lacombe¹,

Wang²,

Pfister‐Guillouzo³

et al. 1992

Inorg. Chem.

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“…Vinylphosphine was the object of great interest since it was synthesized for the first time by Lasnes et al (1) by flashvacuum thermolysis, among other reasons, because it is the phosphorus analog of vinylamine, which constitutes a prototype of unsaturated organic base with a rich and versatile chemistry. On the other hand, this compound could be one of the constituents of the Jupiter and Saturn atmospheres, where vinylphosphine can be formed by the photolysis of PH 3 in the presence of C 2 H 2 (2).…”

Section: Introductionmentioning

confidence: 99%

Vibrational Spectra, DFT Calculations, and Assignments of the syn and the gauche Forms of Vinylphosphine

Bénidar

Doucen

Guillemin

et al. 2001

Journal of Molecular Spectroscopy

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“…We now report the synthesis, by the same method, of vinylphosphine (l), its spectral identification (see ref. 11 for a preliminary communication), and the corresponding tungsten complex. Also described is the preparation and characterization of isopropenylphosphine (2) and prop-I-enylphosphine (3).…”

Section: -Smentioning

confidence: 99%

Retrodienic reactions. Part 2. Vinyl- and propenyl-phosphines: synthesis by flash vacuum thermolysis and characterization

Lasne¹,

Ripoll²,

Thuillier³

1988

J. Chem. Soc., Perkin Trans. 1

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The primary unsaturated phosphines, vinylphosphine (1 ), isopropenylphosphine (2) and ( E ) -prop-1enylphosphine (3) have been synthesized b y flash vacuum thermolysis of their formal Diels-Alder adducts with anthracene, cyclopentadiene, or 1,3-diphenyIisobenzofuran, obtained b y cycloaddition of these dienes with the corresponding dialkyl alkenylphosphonates, followed b y reduction with 1 it hi u m alumini u m hydride-c h lorotrimethylsilane. Compounds (1 )-( 3) were characterized from their spectral data and also as tungsten complex derivatives. The phosphines (1)-(3) exhibit a remarkable and unexpected stability [t; ca. 8 days for ( I ) and 5 days for (2) and (3)] under neutral conditions, in the dark, at room temperature, and were also observed by direct reduction of the corresponding phosphonates in tetrahydrofuran solution.

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Vinylphosphine: synthesis by flash vacuum pyrolysis, stability, and spectroscopic properties

Cited by 19 publications

References 0 publications

Application of photoelectron spectroscopy to molecular properties. 46. Gas-phase structure and stability of alkynylphosphines and allenylphosphines: photoelectronic study

Application of photoelectron spectroscopy to molecular properties. 46. Gas-phase structure and stability of alkynylphosphines and allenylphosphines: photoelectronic study

Vibrational Spectra, DFT Calculations, and Assignments of the syn and the gauche Forms of Vinylphosphine

Retrodienic reactions. Part 2. Vinyl- and propenyl-phosphines: synthesis by flash vacuum thermolysis and characterization

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