Allyltriphenylphosphonium Peroxodisulfate (CH₂˭CHCH₂PPh₃)₂S₂O₈: An Efficient and Convenient Reagent for the Oxidation of Alcohols and Silyl and THP‐Ethers Under Nonaqueous Conditions

References

• House , D. A. 1962 . Kinetics and mechanism of oxidation by peroxidisulfate . Chem. Rev. , 62 : 185
   Web of Science ®Google Scholar
• Firouzabadi , H. , Salehi , P. and Mohammadpoor‐Baltork , I. 1992 . Tetrakis (pyridine) silver(II) peroxidisulfate, [Ag(Py)4]S2O8, a reagent for the oxidative transformation . Bull. Chem. Soc. Jpn. , 65 : 2879
   Google Scholar
• Jung , J. C. , Choi , H. C. and Kim , Y. H. 1993 . Direct facile tetrahyrofuranylation of alcohols through radical coupling with (Bu4N)2S2O8 . Tetrahedron Lett. , 7 : 3581 [CROSSREF]
   Web of Science ®Google Scholar
• Mohammadpoor‐Baltork , I. , Hajipour , A. R. and Mohammadi , H. 1998 . Benzytriphenylphosphonium peroxodisulfate (PhCH2PPh3)2S2O8 a mild and inexpensive reagent for efficient oxidation of organic compounds under nonaqueous and aprotic conditions . Bull. Chem. Soc. Jpn. , 71 : 1649
   Web of Science ®Google Scholar
• Minghu , W. , Guichun , Y. and Zuxing , C. 2000 . Polymer supported peroxodisulfate: a mild and clean oxidation of organic compounds under non aqueous conditions . Synth. Communication , 30 ( 17 ) : 3127
   Web of Science ®Google Scholar
• Green , T. W. and Wutz , P. G.M. 1991 . Protection Group in Organic Synthesis , 2nd Ed. New York : Wiley . Chaps. 2–3
   Google Scholar
• Muzart , J. 1993 . Silyl ethers as protective group for alcohols: oxidative deprotection and stability under oxidation conditions . Synthesis , : 11 and references cited therein [CROSSREF]
   Google Scholar
• Baker , R. , Rao , V. B. , Ravenscroft , P. D. and Swain , C. J. 1983 . Direct conversion of secondary trimethylsilyl ethers to ketones . Synthesis , : 572 [CROSSREF]
   Google Scholar
• Mahrwald , R. , Theil , F. , Schick , H. , Schwartz , S. , Palme , H. J. and Weber , G. 1986 . The oxidation of primary trimethylsilyl ethers to aldehydes—a selective conversion of primary hydroxyl group into an aldehyde group in the presence of a secondary hydroxyl group . J. Prakt. Chem. , 328 : 777 [CROSSREF]
   Google Scholar
• Muzart , J. and N'Ait Ajjaou , A. 1991 . Bis(triphenylsilyl) chromate catalyzed oxidation of silyl ethers by tert‐butyl hydroperoxide . Synlett. , 7 : 497 [CROSSREF]
   Google Scholar
• Olah , G. A. , Gupta , B. G.B. and Fung , A. P. 1980 . Synthetic methods and reactions: ceric ammonium nitrate‐catalyzed oxidative cleavage of alkyl and silyl ethers with sodiom bromate . Synthesis , : 897 [CROSSREF]
   Google Scholar
• Muzart , J. and N'Ait Ajjaou , A. 1992 . Bistriphenylsilanol‐assisted oxidation catalyzed by chromium(VI) oxide of activated trimethylsilyl ethers with tert‐butyl hydroperoxide . Synth. Commun. , 22 : 1993
   Web of Science ®Google Scholar
• Firouzabadi , H. and Mohammadpoor‐Baltork , I. 1994 . Lewis acid prompted reaction (IV): oxidation deprotection of trimethylsilyl ethers with silver and sodium bromates; AgNO3, NaBrO3 . Synth. Commun. , 24 : 1065
   Web of Science ®Google Scholar
• Jung , M. E. 1976 . Oxidation of trimethylsilyl ethers via hydride abstraction. A new method for alcohol oxidation . J. Org. Chem. , 41 : 1479
   Web of Science ®Google Scholar
• Tolstikov , G. A. , Miftakhov , M. S. , Alder , M. E. , Komissarova , N. G. , Kuznetsov , O. M. and Vostrikov , N. S. 1989 . Direct oxidation of alkyl trimethyl‐ and trisilyl ethers to carbonyl compounds. Application to synthesis of prostanoids . Synthesis , : 940 [CROSSREF]
   Google Scholar
• Pinnick , H. W. and Lajis , N. H. 1978 . N‐Bromosuccinimide oxidation of silyl ethers . J. Org. Chem. , 43 : 371
   Google Scholar
• Firouzabadi , H. and Shirini , F. 1996 . Deprotection and direct oxidative deprotection of trimethylsilyl ethers to their corresponding alcohols and carbonyl compounds with tris[trinitratocerium(IV)] para periodate, [(NO3)3Ce]·H2IO6 in an aprotic solvent . Synth. Commun. , 26 : 423
   Web of Science ®Google Scholar
• Firouzabadi , H. and Shirini , F. 1996 . Bis[trinitrato cerium(IV)] chromate: [(NO3)3Ce]2CrO4 vs trinitrato cerium(IV) chromate dihydrate; [(NO3)3Ce]CrO4·2H2O the in oxidation of trimethylsilyl ethers . Synth. Commun. , 26 : 649
   Web of Science ®Google Scholar
• Sarkar , A. , Yemul , O. S. , Bandgar , B. P. , Gaikwad , N. B. and Wadgaonicar , P. P. 1997 . Sulfated zirconia as an efficient catalyst for tetrahydropyranylation and acetalization . Org. Prep. Proced. Int. , 28 : 613
   Google Scholar
• Mohammadpoor‐Baltork , I. and Pouranshiravani , Sh. 1997 . 3‐Carboxypyridinium chlorochromate (CPCC): a mild, efficient and inexpensive reagent for oxidative deprotection of trimethylsilyl ethers and tetrahydropyranyl ether under non‐aqueous conditions . Synthesis , : 756 [CROSSREF]
   Google Scholar
• Heravi , M. M. , Ajami , D. and Gasemzadeh , M. 1999 . Wet alumina supported chromium(VI) oxide: a mild, efficient and inexpensive reagent for oxidative deprotection of trimethylsilyl ethers and tetrahydropyranyl ethers in a solventless system . Synthesis , : 393 [CROSSREF]
   Google Scholar
• Sonnet , P. E. 1978 . Direct conversion of alcohols tetrahydropyranol ethers to aldehydes . Org. Prep. Proced. Int. , 10 : 91
   Web of Science ®Google Scholar
• Parish , E. J. , Kizito , S. A. and Heidepriem , R. W. 1993 . A novel synthesis of steroidal Δ4,3,6‐diones using pyridinium chloro chromate(PCC) . Synth. Commun. , 22 : 223
   Web of Science ®Google Scholar
• Mohammadpoor‐Baltork , I. and Kharamesh , B. 1998 . Oxidative deprotection of tetrahydropyranyl ethers to carbonyl compounds with (4‐dimethylamino)pyridinium and 2,2‐bipyridinium cholorochromates under non aqueous conditions . J. Chem. Research(s). , : 146 [CROSSREF]
   Google Scholar
• Mohammadpoor‐Baltork , I. and Nourozi , A. R. 1999 . Efficient and selective oxidative deprotection of tetrahydropyranyl ethers, ethylene acetals and ketals with silver and sodium bromates in the presence of aluminium chloride . Synthesis , : 487 [CROSSREF]
   Google Scholar
• Wittig and Schollkopf . 1954 . Uber triphenyl‐phosphinmethylene als olefinbildende reagenzien . Chem. Ber. , 87 : 1318
   Google Scholar
• Lakouraj , M. M. and Akbari , A. 2003 . Sulfuric acid supported on silica gel: an efficient catalyst for silylation of hydroxyl groups with HMDS and their convenient deprotection under non‐aqueous condition . Indn. J. Chem. , 42B : 1165
   Google Scholar
• Maity , G. and Chudra , S. 1993 . Ceric ammonium nitrate catalysed protection of alcohols by 3,4‐dihydro‐2H‐pyran . Synth. Commun. , 23 : 1667
   Web of Science ®Google Scholar