User- and eco-friendly hypervalent iodine reagent and method...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof

Reexamination Certificate

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C568S319000, C568S323000, C568S435000, C568S437000, C568S484000

Reexamination Certificate

active

06933405

ABSTRACT:
The present invention is a user- and eco-friendly hypervalent iodine reagent (mIBX) capable of selectively oxidizing allylic and benzylic alcohols in water and other eco-friendly solvents and having generally the following structure:Allylic and benzylic alcohols are cleanly oxidized to the corresponding carbonyl compounds in water or water-THF mixtures, or other mixtures, using a water-soluble o-iodoxybenzoic acid derivative of the present invention.

REFERENCES:
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Togo, Hideo, et al.; Preparation and Reactivities of Novel (Diacetoxyiodo)arenes Bearing Heteroaromatics; J. Org. Chem; 2000; pp. 8391-8394; vol. 65; American Chemical Society; USA.
Frish, Limor, et al.; A Pulsed Gradient Spin Echo NMR Study of Guest Encapsulation by Hydrogen-Bonded Tetraurea Calix[4]arene Dimers; J. Chem. Soc., Perkin Trans. 2; 1999; pp. 669-671.
De Mico, Antonella, et al.: A Versatile and Highly Selective Hypervalent Iodine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds; J. Org. Chem; 1997; pp. 6974-6977; vol./Issue 62; American Chemical Society; USA.
Frigerio, Marco, et al.; Oxidation of Alcohols With o-Iodoxybenzoic Acid (IBX) in DMSO: A New Insight into an Old Hypervalent Iodine Reagent; J. Org. Chem.; 1995; vol./Issue 60; pp. 7272-7276; American Chemical Society: USA.
Dess, Daniel B., et al.; A Useful 12-I-5 Triacetoxyperiodinane (the Dess-Martin Periodinane) for the Selective Oxidation of Primary or Secondary Alcohols and a Variety of Related 12-I-5 SpeciesIa; J. Am. Chem. Soc.; 1991; vol./Issue 113; pp. 7277-7287; American Chemical Society; USA.
Dess, D.B., et al.; Readily Accessible 12-I-5IOxidant for the Conversion of Primary and Secondary Alcohols to Aldehydes and Ketones; J. Org. Chem.; 1983; vol./Issue 48; pp. 4155-4156; American Chemical Society; USA.
Meyer, Stephanie D., et al.; Accelleration of the Dess-Martin Oxidation by Water; J. Org. Chem.; 1994; vol./Issue 59; pp. 7549-7552; American Chemical Society; USA.
Frigerio, Marco, et al.; A User-Friendly Entry to 2-Iodoxybenzoic Acid (IBX); J. Org. Chem.; 1999; vol./Issue 64; pp. 4537-4538; American Chemical Society; USA.
Nicolaou, K.C., et al.; New Synthetic Technology for the Construction of N-Containing Quinones and Derivatives Thereof; Total Synthesis of Epoxyquinomycin B; Angew. Chem. Int. Ed.; 2001; pp. 207-210;vol. 40; Issue 1; Wiley-VCH Verlag GmbH; Weinheim Germany.
Nicolaou, K.C., et al.; New Synthetic Technology for the Rapid Construction of Novel Heterocycles—Part 1: The Reactoin of Dess-Martin Periodinane with Anilides and Related Compounds; Angew. Chem. Int. Ed.; 2000; pp. 622-625; vol. 39; Issue 3; Wiley-VCH Verlag GmbH; Weinheim Germany.
Nicolaou, K.C., et al.; New Synthetic Technology for the Rapid Construction of Novel Heterocycles—Part 2: The Reaction of IBX with Anilides and Related Compounds; Angew. Chem. Int. Ed.; 2000; vol. 39; Issue 3; p. 625-628, Wiley-VCH Verlag GmbH; Weinheim Germany.
Nicolaou, K.C., et al; Novel IBX-Mediated Processes for the Synthesis of Amino Sugars and Libraries Thereof; Angew. Chem. Int. Ed.; 2000; pp. 2525-2529; vol. 39; Issue 14; Wiley-VCH Verlag GmbH; Weinheim Germany.
Nicolaou, K.C., et al.; A New Method for the One-Step Synthesis of αβ-Unsaturated Carbonyl Systems from Saturated Alcohols and Carbonyl Compounds; J. Am. Chem. Soc.; 2000; pp. 7596-7597; vol./Issue 122; American Chemical Society; USA.
Nicolaou, K.C. et al.; Selective Oxidation of Carbon Adjacent to Aromatic Systems with IBX; J. Am. Chem. Soc.; 2001; pp. 3183-3185; vol./Issue 123; American Society; USA.
Ritter, Stephen K.; Green Chemistry; Chemical & Engineering News; Jul. 16, 2001; pp. 27-34; USA.
Li/ Chao-Jun; Organic Reactions in Aqueous Media—With Focus on Carbon-Carbon Bond Formation; Chem. Rev.; 1993; pp. 2023-2035; vol./Issue 93; American Chemical Society; USA.

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