ISSN:
0009-2940
Keywords:
1-Alken-3-ynes
;
Manganese(III) acetate
;
Propargyl radical
;
Ligand-transfer reaction
;
Electron-transfer reaction
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Control of the Propargylic Radical Stabilization by Carbon-Chain Length in Manganese(III)-Mediated Reactions of 1-Alken-3-ynes. - A Facile Synthetic Way to Long-Chain 4-Acetoxy-5-alkynoic AcidsBy investigation of reactions of 1-alken-3-ynes RC ≡ C - CH = CH2 4 with acetic acid/acetic anhydride, mediated by manganese(III) acetate, it has been found that the stabilization of propargylic radical adducts depends on the carbon-chain length of R in 4. R = C8H17 is shown to be the “critical” chain length when ligand transfer reaction appears to be the only way of stabilization of intermediates, thus providing a facile one-step access to long-chain 4-acetoxy-5-alkynoic acids. The dependence of the product ratios on the AcOH/Ac2O ratio has also been demonstrated.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19911240926
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