Woodward cis-hydroxylation

Woodward cis-hydroxylation
Named after Robert Burns Woodward
Reaction type addition reaction
Identifiers
Organic Chemistry Portal woodward-reaction

The Woodward cis-hydroxylation (also known as the Woodward reaction) is the chemical reaction of alkenes with iodine and silver acetate in wet acetic acid to form cis-diols.[1][2](conversion of olefin into cis-diol)

The reaction is named after its discoverer, Robert Burns Woodward.

The Woodward cis-hydroxylation
The Woodward cis-hydroxylation

This reaction has found application in steroid synthesis.[3]

  1. ^ Woodward, R. B., U.S. patent 2,687,435
  2. ^ Woodward, R. B.; Brutcher, F. V. (1958). "cis-Hydroxylation of a Synthetic Steroid Intermediate with Iodine, Silver Acetate and Wet Acetic Acid". J. Am. Chem. Soc. 80 (1): 209–211. doi:10.1021/ja01534a053. ISSN 0002-7863.
  3. ^ Mangoni, L.; Dovinola, V. (1969). "The stereochemistry of woodward cis-hydroxylation in some steroidal olefins". Tetrahedron Letters. 10 (60): 5235–5238. doi:10.1016/S0040-4039(01)88931-0. ISSN 0040-4039.