Hydrazides are selectively oxidised to esters/acids in high yields using Oxone® in the presence of an appropriate alcohol/water as a nucleophile at ambient temperature. A variety of functional groups including alkenes, alcohols, ethers, cyclopropyl groups and nitriles are unaffected.
References
1.
(a) KocevarM., SusinP., and PolancS., Synthesis, 1993, 773–774
2.
KocevarM., MihorkoP., and PolancS., Synlett, 1995, 241–242
3.
KosmrljJ., KocevarM., and PolancS., Synlett, 1996, 652–654
4.
KepeV., PozganF., GolobicA., PolancS., and KocevarM., J. Chem. Soc., Perkin Trans. 1, 1998, 2813–2816.
5.
RigoB., and CouturierD., J. Heterocyclic Chem., 1986, 23, 253 and references cited therein.
6.
(a) AylwardJ.B., and NormanR. O. C., J. Chem. Soc.(C), 1968, 2399.
7.
TsujiJ., HayakawaS., and TakayanagiH., Chem. Lett., 1975, 437.
8.
TsujiJ., NagashimaT., QuiN. T., and TakayanagiH., Tetrahedron, 1980, 36, 1311
9.
BackT.G., CollinsS., and KerrR. G., J. Org. Chem., 1981, 46, 1564
10.
HoffmanR.V., and KumarA., J. Org. Chem., 1984, 49, 4014.
11.
GladstoneW.A. F., J. Chem. Soc.(C), 1969, 1571.
12.
StefaneB., KocevarM., and PolancS., J. Org. Chem., 1997, 62, 7165–7169.
13.
KocevarM., MihorkoP., and PolancS., J. Org. Chem., 1995, 60, 1466–1469.
14.
(a) StefaneB., KocevarM., and PolancS., Tetrahedron Lett., 1999, 40, 4429–4432
15.
HoT.L., HoH. C., and WongC. M., Synthesis, 1972, 562–563.
16.
PrakashO., SharmaV., and SadanaA., J. Chem. Res.(S), 1996, 100–101.
17.
WebbK.S., and RuszkayS. J., Tetrahedron., 1998, 54, 401 and references cited therein.
18.
Dictionary of Organic Compounds, 1996, 6th edn. Chapman & Hall. IICT Communication No. 4409.
