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Synthesis and solid state structures of Chalcogenide compounds of Imidazolin-2-ylidene-1,1-Diphenyl-phosphinamine

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Abstract

We report the synthesis and solid state structures of 1,3-di-aryl-imidazolin-2-ylidine-1,1-diphenylphosphinamine [(aryl = mesityl (1a) and aryl = 2,6-diisopripyl (1b)] and their chalcogenide compounds 1, 3-di-aryl-imidazolin-2-ylidine- P,P-diphenylphosphinicamide (2a,b), 1,3-di-aryl-imidazolin-2-ylidine-P,P-diphenyl-phosphinothioicamide (3a,b) and 1,3-diaryl-imidazolin-2-ylidine- P,P-diphenyl-phosphinoselenoic-amide (4a,b). The compounds 1a,b were prepared in good yield by the reaction of 1,3-di-aryl-imidazolin-2-imine and chlorodiphenylphosphine in the presence of triethylamine in toluene. The reactions of 1a,b with elemental sulphur and selenium afforded the corresponding chalcogenide compounds 3a,b and 4a,b respectively. The corresponding oxo- derivative (2a,b) was obtained by reacting compound 1a,b with 30% aqueous hydrogen peroxide in THF. The molecular structures of 1a, 2a, 3a and 4a,b have been established by single crystal X-ray diffraction analyses. The molecular structures reveal that even C1–N1–P1 angle (124.62 ∘) in compound 1a is less obtuse compared to the corresponding C1–N1–Si1 angles (157.8 ∘) observed in related N-silylated 2-iminoimidazolines and trimethylsilyl iminophosphoranes. C1–N1–P1 angles are further widened in compounds 2a, 3a, and 4a,b due to the attachment of chalcogen atoms onto phosphorus atom.

We report the synthesis and structural characterization of 1,3-di-aryl-imidazolin-2-ylidine-1,1-diphenylphosphinamine, [ImRNPPh2] and their respective chalcogenide compounds, ImRNP(=E)Ph2 [E= O, R = Mes, (2a), Dipp (2b); E = S, R = Mes, (3a), Dipp (3b); E = Se, R = Mes, (4a), Dipp (4b)].

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Acknowledgements

This work is supported by the Ministry of New and Renewable Energy (MNRE), India under project no. 103/209/2013-NT, dated 29 th September, 2014. The instrumental facilities were provided by the Indian Institute of Technology Hyderabad (IITH). K N thanks University Grants Commission, India, for the PhD fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, 502 285, Sangareddy, Telangana, India

    KISHOR NAKTODE, SUMAN DAS, ABHINANDA KUNDU & TARUN K PANDA

  2. Department of Applied Chemistry, Indian School of Mines, Dhanbad, 826 004, Jharkhand, India

    HARI PADA NAYEK

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  1. KISHOR NAKTODE
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  2. SUMAN DAS
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Correspondence to TARUN K PANDA.

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Supplementary Information (SI)

The 1H and 31 P{1H}NMR spectra of compounds 1a, 1b, 2a, 2b, 3a, 3b, 4a and 4b are given in Supplementary Information, available at www.ias.ac.in/chemsci.

This work is dedicated to Prof. Dr. Peter W. Roesky on the occasion of his 49th Birthday

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NAKTODE, K., DAS, S., KUNDU, A. et al. Synthesis and solid state structures of Chalcogenide compounds of Imidazolin-2-ylidene-1,1-Diphenyl-phosphinamine. J Chem Sci 128, 373–382 (2016). https://doi.org/10.1007/s12039-015-1031-7

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