Milas hydroxylation

The Milas-hydroxylation is a name reaction of organic chemistry , which goes back to Nicholas A. Milas and Sidney Sussman. The reaction was first published in 1936 as a synthesis for the production of cis diols .

Overview reaction

The Milas hydroxylation is an oxidation reaction between an alkene ( 1 ) and hydrogen peroxide to form a cis -diol ( 2 ) in the presence of e.g. B. catalytic amounts of osmium tetroxide (OsO ₄ ) .

Reaction mechanism

A possible reaction mechanism for Milas hydroxylation is described by Zerong Wang as follows:

The hydrogen peroxide ( 1 ) forms an intermediate product ( 3 ) with the catalyst osmium tetroxide (OsO ₄ ) ( 2 ), which reacts with the alkene after the rearrangement and forms another intermediate product. Subsequent cleavage of OsO ₄ results in the cis diol ( 4 ).

application

Milas hydroxylation is used in preparative chemistry .

See also

Dihydroxylation , Sharpless dihydroxylation , Prévost hydroxylation

Web links

Commons : Milas hydroxylation  - collection of images, videos and audio files

Individual evidence

1. ↑ ^{a b c d e} Zerong Wang: Comprehensive Organic Name Reactions and Reagents, Volume 2 . John Wiley, Hoboken (NJ) 2009, ISBN 978-0-470-28662-3 , pp. 1948-1951 .