Phosphaalkene

Source: Wikipedia, the free encyclopedia.
Not to be confused with diphosphenes.
Ball-and-stick model of mesityldiphenylmethylenephosphine, a phosphaalkene

Phosphaalkenes (

Diels-Alder reactions
.

The first phosphaalkene discovered was a

keto-enol tautomerism akin a Brook rearrangement
:

Becker reaction to phosphaalkenes (R = methyl or phenyl)

In the same year

DBU, DABCO or triethylamine:[2]

Phosphaalkene general method

The Becker method is used in the synthesis of the phosphorus pendant of Poly(p-phenylene vinylene):[3]

Poly(p-phenylenephosphaalkene).

The reduction or oxidation of phosphaalkenes can produce radical phosphorus ions.

References

  1. ^ Bildung und Eigenschaften von Acylphosphinen. I. Monosubstitutionsreaktionen an substituierten Disilylphosphinen mit Pivaloylchlorid Gerd Becker, Zeitschrift für anorganische und allgemeine Chemie 1976, 423, pp 242 - 254
  2. ^ Synthesis of mesityldiphenylmethylenephosphine: a stable compound with a localized phosphorus:carbon bond T. C. Klebach, R. Lourens, F. Bickelhaupt
    doi:10.1021/ja00483a041
  3. doi:10.1021/ja060816l
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