Regiochemical Reversals in Nitrosobenzene Reactions with Carbonyl Compounds - α-Aminooxy Ketone versus α-Hydroxyamino Ketone Products

The Lewis acid catalyzed reaction of nitrosobenzene with a ketone can produce an α‐aminooxy ketone or an α‐hydroxyamino ketone; the reaction regiochemistry switches from the latter to the former upon the addition of a Lewis acid or sterically‐hindered solvent. Whereas the latter (C–N bond formation)...

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Published in	European journal of organic chemistry Vol. 2012; no. 30; pp. 6013 - 6020
Main Authors	Nelson, Donna J., Kumar, Ravi, Shagufta
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 01.10.2012 WILEY‐VCH Verlag Wiley-VCH
Subjects	Catalysis Catalysts: preparations and properties Chemistry Enolate chemistry Exact sciences and technology General and physical chemistry Kinetics and mechanisms Lewis acids Noncondensed benzenic compounds Organic chemistry Preparations and properties Reaction mechanisms Reactivity and mechanisms Regioselectivity Sigmatropic rearrangement Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Lewis acid Sigmatropic reaction Hydroxylamine Regioselectivity Theoretical study Lewis acids Steric hindrance Acid catalysis Enolate chemistry Sigmatropic rearrangement Ketone HSAB principle Carbonyl Compounds Reaction mechanism Benzenic compound Acetic acid Reaction mechanisms Enolate Solvent Catalyst Nucleophile
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Abstract	The Lewis acid catalyzed reaction of nitrosobenzene with a ketone can produce an α‐aminooxy ketone or an α‐hydroxyamino ketone; the reaction regiochemistry switches from the latter to the former upon the addition of a Lewis acid or sterically‐hindered solvent. Whereas the latter (C–N bond formation) is easily explained by attack of the enolate α‐carbon at the N atom, the former (C–O bond formation) has been an enigma, with few proposed explanations, and none that explains the simultaneous formation of both products and all the regiochemical reversals. Herein, the regiochemistry reversal is proposed to occur by (1) nucleophile formation governed by hard and soft acids and bases (HSAB) theory, (2) a nucleophilic attack by the enolate O atom at the N atom, followed by (3) a [2,3]‐sigmatropic rearrangement. This mechanistic pathway and HSAB considerations account for the formation of both products and explain the three reported regiochemistry reversals, which are observed upon the introduction of (A) Lewis acid catalyst, (B) AcOH, or (C) solvent bulkiness. A simple and reasonable mechanism for the Lewis acid catalyzed reaction of nitrosobenzene with a ketone or enamine to form an α‐aminooxy ketone (C–O, as opposed to C–N, bond formation) is proposed, and the reaction occurs by initial nucleophilic attack on Ph–N=O, which is governed by the principles of hard and soft acids and bases theory, followed by a [2,3]‐sigmatropic rearrangement.
AbstractList	Abstract The Lewis acid catalyzed reaction of nitrosobenzene with a ketone can produce an α‐aminooxy ketone or an α‐hydroxyamino ketone; the reaction regiochemistry switches from the latter to the former upon the addition of a Lewis acid or sterically‐hindered solvent. Whereas the latter (C–N bond formation) is easily explained by attack of the enolate α‐carbon at the N atom, the former (C–O bond formation) has been an enigma, with few proposed explanations, and none that explains the simultaneous formation of both products and all the regiochemical reversals. Herein, the regiochemistry reversal is proposed to occur by (1) nucleophile formation governed by hard and soft acids and bases (HSAB) theory, (2) a nucleophilic attack by the enolate O atom at the N atom, followed by (3) a [2,3]‐sigmatropic rearrangement. This mechanistic pathway and HSAB considerations account for the formation of both products and explain the three reported regiochemistry reversals, which are observed upon the introduction of (A) Lewis acid catalyst, (B) AcOH, or (C) solvent bulkiness. The Lewis acid catalyzed reaction of nitrosobenzene with a ketone can produce an α‐aminooxy ketone or an α‐hydroxyamino ketone; the reaction regiochemistry switches from the latter to the former upon the addition of a Lewis acid or sterically‐hindered solvent. Whereas the latter (C–N bond formation) is easily explained by attack of the enolate α‐carbon at the N atom, the former (C–O bond formation) has been an enigma, with few proposed explanations, and none that explains the simultaneous formation of both products and all the regiochemical reversals. Herein, the regiochemistry reversal is proposed to occur by (1) nucleophile formation governed by hard and soft acids and bases (HSAB) theory, (2) a nucleophilic attack by the enolate O atom at the N atom, followed by (3) a [2,3]‐sigmatropic rearrangement. This mechanistic pathway and HSAB considerations account for the formation of both products and explain the three reported regiochemistry reversals, which are observed upon the introduction of (A) Lewis acid catalyst, (B) AcOH, or (C) solvent bulkiness. A simple and reasonable mechanism for the Lewis acid catalyzed reaction of nitrosobenzene with a ketone or enamine to form an α‐aminooxy ketone (C–O, as opposed to C–N, bond formation) is proposed, and the reaction occurs by initial nucleophilic attack on Ph–N=O, which is governed by the principles of hard and soft acids and bases theory, followed by a [2,3]‐sigmatropic rearrangement.
Author	Nelson, Donna J. Shagufta Kumar, Ravi
Author_xml	– sequence: 1 givenname: Donna J. surname: Nelson fullname: Nelson, Donna J. email: djnelson@ou.edu organization: Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA, Fax: +1-405-325-6111, http://faculty-staff.ou.edu/N/Donna.J.Nelson-1/ – sequence: 2 givenname: Ravi surname: Kumar fullname: Kumar, Ravi organization: Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA, Fax: +1-405-325-6111, http://faculty-staff.ou.edu/N/Donna.J.Nelson-1/ – sequence: 3 surname: Shagufta fullname: Shagufta organization: Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA, Fax: +1-405-325-6111, http://faculty-staff.ou.edu/N/Donna.J.Nelson-1/
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Keywords	Lewis acid Sigmatropic reaction Hydroxylamine Regioselectivity Theoretical study Lewis acids Steric hindrance Acid catalysis Enolate chemistry Sigmatropic rearrangement Ketone HSAB principle Carbonyl Compounds Reaction mechanism Benzenic compound Acetic acid Reaction mechanisms Enolate Solvent Catalyst Nucleophile
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Snippet	The Lewis acid catalyzed reaction of nitrosobenzene with a ketone can produce an α‐aminooxy ketone or an α‐hydroxyamino ketone; the reaction regiochemistry... Abstract The Lewis acid catalyzed reaction of nitrosobenzene with a ketone can produce an α‐aminooxy ketone or an α‐hydroxyamino ketone; the reaction...
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SubjectTerms	Catalysis Catalysts: preparations and properties Chemistry Enolate chemistry Exact sciences and technology General and physical chemistry Kinetics and mechanisms Lewis acids Noncondensed benzenic compounds Organic chemistry Preparations and properties Reaction mechanisms Reactivity and mechanisms Regioselectivity Sigmatropic rearrangement Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Title	Regiochemical Reversals in Nitrosobenzene Reactions with Carbonyl Compounds - α-Aminooxy Ketone versus α-Hydroxyamino Ketone Products
URI	https://api.istex.fr/ark:/67375/WNG-2W1N2FMS-Q/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fejoc.201200893
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