Hi guyz.
I think this Mn(OAc)3 it's more interesting than someone would expect.
From Advanced Organic Chemistry, J. March, 4th edition, page 835-6, section 5-45
The conversion of olefines to gamma-lactones (Addition of Oxygen, Carbon)
Global rxn:
>C=C< + Mn(OAc)3 =(HOAc)=> 3,4-(substituted)gamma-lactone
Olefins react with manganese (III) acetate to give gamma-lactones(1). The mechanism is probably free-radical, involving addition of .CH2COOH to the double bond. Lactone formation has also been accomplished by treatment of olefins with lead tetraacetate(2), with a alpha-bromocarboxylic acids in the presence of benzoyl peroxide as catalyst(3), and with dialkyl malonates and iron (III) perchlorate Fe(ClO4)3.9H2(4). Olefins can also be converted to gamma-lactone by indirect routes(4).
So, if you use ethylene, acetic acid and the magic Mn(OAc)3, you can product GBL and then GHB!
Refs:
(1) JACS 90:5903(1968), 90:5905(1968), 96:7977(1974)
JCS, Perkin Trans 2 1537(1984)
Tetrahedron 47:831(1991)
Tetrahedron Lett. 26:3761(1985), 26:4291(1985)
(2) JACS 90:2706(1968)
(3) Bull. Chem. Soc. Jpn. 60:1049(1987)
Tetrahedron Lett. 25:3939(1984)
(4) Synlett 42:(1990)
(5) Chem. Ber. 102:4157(1969)
Helv. Chem. Acta 55:2198(1972)
Tetrahedron Lett. 29:6925(1988)