RSS-Feed abonnieren
DOI: 10.1055/s-0029-1219570
Benzyltriphenylphosphonium Peroxymonosulfate
Publikationsverlauf
Publikationsdatum:
10. März 2010 (online)
![](https://www.thieme-connect.de/media/synlett/201006/lookinside/thumbnails/10.1055-s-0029-1219570-1.jpg)
Introduction
Benzyltriphenylphosphonium peroxymonosulfate (1, BTPPMS) is a mild, efficient, stable, and cheap reagent which displays its versatility in organic synthesis. It is a white solid and generally stored at room temperature. It is quite soluble in dichloromethane, chloroform, acetone, and acetonitrile but insoluble in non-polar solvents, such as carbon tetrachloride, n-hexane, and diethyl ether. It has been used for the oxidation of alcohols to aldehydes and ketones under aprotic solvent condition, [¹] oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers under non-aqueous conditions, [²] and selective oxidation of sulfides and thiols to the corresponding sulfoxides and disulfides under solvent-free conditions. [³] It was also found to be useful for the dethioacetalization of 1,3-dithiolanes and 1,3-dithianes to the corresponding carbonyl compounds in the presence of bismuth chloride under aprotic conditions [4] and conversion of oximes and semicarbazones to carbonyl compounds using microwave irradiation to afford the carbonyl compounds. [5] Because of the mild conditions as well as the high yields, this reagent has wide acceptance in the area of synthetic chemistry.
- 1
Hajipour AR.Mallakpour SE.Adibi H. Phosphorus Sulfur Silicon Relat. Elem. 2000, 167: 71 - 2
Hajipour AR.Mallakpour SE.Mohammadpoor-Baltork I.Adibi H. Phosphorus Sulfur Silicon Relat. Elem. 2000, 165: 155 - 3
Hajipour AR.Mallakpour SE.Adibi H. Phosphorus Sulfur Silicon Relat. Elem. 2002, 177: 2277 - 4
Hajipour AR.Mallakpour SE.Mohammadpoor-Baltork I.Adibi H. Phosphorus Sulfur Silicon Relat. Elem. 2002, 177: 2805 - 5
Hajipour AR.Mallakpour SE.Mohammadpoor-Baltork I.Adibi H. Monatsh. Chem. 2003, 134: 45 -
6a
Hajipour AR.Mallakpour SE.Adibi H. Chem. Lett. 2000, 460 -
6b
Hajipour AR.Mallakpour SE.Mohammadpoor-Baltork I.Adibi H. Synth. Commun. 2001, 31: 1625 -
6c
Hajipour AR.Mallakpour SE.Mohammadpoor-Baltork I.Adibi H. Synth. Commun. 2001, 31: 3401 - 7
Trost BM.Braslau R. J. Org. Chem. 1988, 53: 532 - 8
Hajipour AR.Mallakpour SE.Adibi H. Chem. Lett. 2001, 164 - 9
Hajipour AR.Mallakpour SE.Mohammadpoor-Baltork I.Adibi H. Molecules 2002, 7: 674 - 10
Hajipour AR.Mallakpour SE.Adibi H. J. Org. Chem. 2002, 67: 8666 - 11
Adibi H.Hajipour AR.Hashemi M. Tetrahedron Lett. 2007, 48: 1255 - 12
Adibi H.Hajipour AR. Bioorg. Med. Chem. Lett. 2007, 17: 1008 - 13
Adibi H.Hajipour AR.Jafari H. Chem. Heterocycl. Compds. 2008, 44: 802