Milas hydroxylation

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The Milas hydroxylation is an organic reaction converting an alkene to a vicinal diol, and was developed by Nicholas A. Milas in the 1930s.[1][2] The cis-diol is formed by reaction of alkenes with hydrogen peroxide and either ultraviolet light or a catalytic osmium tetroxide,[3] vanadium oxide, or chromium oxide.[4]

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The reaction has been superseded in synthetic chemistry by the Upjohn dihydroxylation and later by the Sharpless asymmetric dihydroxylation.


  1. ^ Milas, Nicholas A.; Sussman, Sidney (July 1936). "The Hydroxylation of the Double Bond". Journal of the American Chemical Society. 58 (7): 1302–1304. doi:10.1021/ja01298a065. 
  2. ^ "Milas Hydroxylation". Comprehensive Organic Name Reactions and Reagents. 437: 1948–1951. 2010. doi:10.1002/9780470638859.conrr437. 
  3. ^ Milas, Nicholas A.; Trepagnier, Joseph H.; Nolan, John T.; Iliopulos, Miltiadis I. (September 1959). "A Study of the Hydroxylation of Olefins and the Reaction of Osmium Tetroxide with 1,2-Glycols". Journal of the American Chemical Society. 81 (17): 4730–4733. doi:10.1021/ja01526a070. 
  4. ^ Milas, Nicholas A. (November 1937). "The Hydroxylation of Unsaturated Substances. III. The Use of Vanadium Pentoxide and Chromium Trioxide as Catalysts of Hydroxylation". Journal of the American Chemical Society. 59 (11): 2342–2344. doi:10.1021/ja01290a072.