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Synthesis 1987; 1987(8): 689-693
DOI: 10.1055/s-1987-28046
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Unusually Coordinated Phosphorus Compounds; 22.1 Cycloaddition Reactions of Nitrilium Betaines with a Stable Phosphaalkyne

W. Rösch* , M. Regitz
  • *Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schrödinger-Straße, D-6750 Kaiserslautern, West Germany
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Publikationsdatum:
12. September 2002 (online)

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(2,2-Dimethylpropylidyne)phosphane (7) undergoes regiospecific [3 + 2]-cycloaddition reactions with the arylnitrile oxides 2a-c to yield the 1,2,4-oxazaphospholes 8a-c. In the reaction of phosphaalkyne 7 with 2,2-dimethylpropanenitrile oxide (2d) the 1:2-adduct 10 is formed in addition to 8d. The reaction of 7 with the nitrile sulphide 12 produces the 1,2,4-thiazaphosphole 13. The 1H-1,2,4-diazaphospholes 18a-c are obtained from the reactions of 7 with the nitrile imines 17a-c; the regioisomers 21a and 21b have been detected by NMR spectroscopy.