Calcium-mediated Hydrophosphorylation of Organic Isocyanates with Diphenylphosphane Oxide
Stephan Härling A , Julia Greiser A , Tareq M. A. Al-Shboul A , Helmar Görls A , Sven Krieck A and Matthias Westerhausen A B
+ Author Affiliations
- Author Affiliations
A Institute of Inorganic and Analytical Chemistry, Friedrich Schiller University Jena, Humboldtstrasse 8, D-07743 Jena, Germany.
B Corresponding author. Email: m.we@uni-jena.de
Australian Journal of Chemistry 66(10) 1264-1273 https://doi.org/10.1071/CH13259
Submitted: 17 May 2013 Accepted: 1 July 2013 Published: 21 August 2013
Abstract
The calcium-mediated addition of diphenylphosphane oxide to organic isocyanates and isothiocyanates yields N-alkyl and N-aryl substituted diphenylphosphorylformamides (E = O, R = iPr, tBu, cHex, Ph, C6H4-4-Br, C6H2-2,4,6-Me3, and Naph) and -thioformamides (E = S, R = iPr, cHex, Ph, and C6H4-4-Me), respectively, of the type Ph2P(O)–C(E)–N(H)R. All derivatives were characterized by IR and NMR spectroscopy as well as X-ray diffraction experiments. The wavenumbers of the N–H stretching modes are smaller for the thio analogues and N-aryl substituents. In the solid state all formamides and thioformamides form dimers by N–H⋯O–P hydrogen bridges. The P–CCE bonds are significantly elongated compared with the P–CPh distances.
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