Oxidation in organophosphorus chemistry: Potassium peroxymonosulphate

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2637-2640

  Woźniak, Lucyna A ^a   Stec, Wojciech J ^a  

^a POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

Phosphorus compounds; Stereospecific oxygenation

Indexed keywords

PEROXYSULPHATE POTASSIUM; PHOSPHOROTHIOIC ACID DERIVATIVE; PHOSPHOROTHIOIC ACID O,O,S TRIMETHYL ESTER; PHOSPHORUS DERIVATIVE; POTASSIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; CONFORMATIONAL TRANSITION; ORGANIC CHEMISTRY; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION;

EID: 0033605913     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00261-0     Document Type: Article

References (11)

1. Stec WJ, Woźniak LA, Pyzowski J, Niewiarowski W. Antisense and Nucleic Acid Drug Develop. 1997;7:381-395.
2. Benner et al. successfuly used oxone solution for conversion of Sulfides to corresponding sulfoxides and/or sulfones without affecting of nucleoside residues present in their compounds: Huang Z, Schneider KC, Benner SA. J.org.chem. 1991;56:3869-3882.
3. Roughton L, Potmann S, Benner SA, Egli M. J.Am.Chem.Soc. 1995;117:7249-7250.
4. 3P(O), and some negative attempts presented by Thompson et al., to our best knowledge there has been no data published about the oxidizing properties of Caro's acid towards organophosphorus compounds: Kennedy RJ, Stock AM. J.Org.Chem. 1960;25:1901-1906.
5. Jackson JA, Berkman CE, Thompson CM. Tetrahedron Lett. 1992;33:6061-6064.
6. Oxidative detoxification of phosphonothiolates, Yang Y-C, Szafraniec LL, Beaudry WT, Rohrbaugh DK. J.Am.Chem.Soc. 1990;112:6621-6627.
7. Wieczorek M, Majzner WR, KaczmaRek R, Baraniak J, Stec WJ. Heteroatom Chem. 1998;9:271-276.
8. 3P], or were prepared via methods described elsewhere.
9. Stec WJ, Okruszek A. J.Chem.Soc., Perkin Trans. 1, 1975: 1828.
10. Woźniak LA, Kobylańska A, Koziolkiewicz M, Stec WJ. Bioorg.Med.Chem.Lett. 1998,8:2641-2646.
11. Complete data of conversions of P(III), P(S), and P(Se) to the corresponding P(O) compounds have recently been presented by Gilchrist, TL, in Trost BM, Fleming I, Editors. Comprehensive Organic Synthesis, Vol 7, Pergamon Press 1991, Pp 752-756.