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BaMnO4 Oxidation of Primary and Secondary Alcohols

Mechanism + Description

Mechanism unclear- probably coordination to the MnVI atom followed by elimination of the ketone and formation of MnIV

General comments

Barium manganate has been reported as a reagent for the synthesis of aldehydes and ketones, It is said to be more reproducible than MnO2, but appears to be little used.  Ba(MnO4)2 is an easily prepd., stable, and a versatile oxidn. reagent. With this reagent different types of primary and secondary hydroxy compds. are converted to carbonyl derivs. Aldehydes could be transformed to carboxylic acids. Benzylic chlorides and bromides are converted to aldehydes and carboxylic acids.  Soluble Barium salts are acutely toxic

Key references

Selective oxidation of alcohols by manganates Tetrahedron Letters (1989), 30(19), 2559-62.

Barium Manganate: An efficient oxidising reagent for oxidation of primary and secondary alcohols to carbonyl compounds  Tetrahedron Letters (1978), (9), 839-40.

Barium Manganate. A Versatile Oxidant in Organic Synthesis ; Bull. Chem. Soc. Jpn. 56 (3): 914–17,

Barium Permangante, Ba(MnO4)2, a versatile and mild oxidizing agent for use under aprotic and non-aqueous conditions ; Tetrahedron (1990), 46(19), 6869-78.

Relevant scale up example

No scale up examples identified