Barton Vinyl Iodide Synthesis

Barton Vinyl Iodide Synthesis

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  • Generality
  • Reagent Availability
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  • General Characteristics

Hydrazones can be converted into vinyl iodides using molecular iodine under mild conditions. Vinyl selenides can be synthesized as well in similar manner using reagents such as PhSeBr.

  • General References

  • Reaction Mechanism

Barton_vinylI_2.gif

  • Examples

An example within the context of cortistatin A synthesis.[1]

Barton_vinylI_3.gif

An application to ouabagenin synthesis.[2]

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  • Experimental Tips

  • References

[1] Lee, H. M.; Nieto-Oberhuber, C.; Shair, M. D. J. Am. Chem. Soc. 2008, 130, 16864. DOI: 10.1021/ja8071918 [2] Renata, H.; Zhou, Q.; Baran, P.S. Science, 2013, 339, 59. DOI: 10.1126/science.1230631

  • Related Reactions

  • Related Books

  • External Links

Hydrazone Iodination – Wikipedia

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