PEYOTE (Hive Bee)
10-17-01 19:14
No 225843
      Easy GBL  Bookmark   

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!

(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)
(Chief Bee)
10-17-01 20:25
No 225858
      Re: Easy GBL  Bookmark   

The alkene you would use for GBL would be ethene... Not easy to handle, as it is a gas. But it is probably of more use for substituted GBL's.
(Hive Bee)
10-19-01 02:43
No 226520
      Re: Easy GBL  Bookmark   

yes, however, of ethene was cleaveged in situ, and the
manganese (III) acetate was deposited as a catalytic
stack of mesh, and the ethene passed through this stack,
would this be an appropriate method for converting the
olefin in the vapour phase?

Don't mind me. I'm mentally ill.