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Polar Acetalization and Transacetalization in the Gas Phase: The Eberlin Reaction†
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Section:- 1. Introduction
- 2. Experimental and Theoretical Methods
- 3. Prototype Eberlin Reaction
- 3.1. Reaction Mechanism
- 3.2. Reaction Efficiency and Regioselectivity
- 3.3. Relationship to Condensed-Phase Reactions
- 3.4. Related Ion/Molecule Reactions
- 4. Scope of the Eberlin Reaction
- 4.1. Carboxonium Ions and Related Reagents
- 4.2. Borinium Ions
- 4.3. Sulfinyl Ions and Arylsulfenium Ions
- 4.4. Silylium Ions
- 4.5. Phosphonium Ions
- 4.6. Arylnitrenium Ions
- 4.7. Nitronium Ion
- 4.8. Hetarynium Ions
- 4.9. Distonic and Distonoid Acylium Ions
- 5. Applications
- 5.1. Gas-Phase Synthesis5.1.1. Synthesis of Heterocycles
- 5.1.2. Interconversion of Sulfur and Oxygen Ions
- 5.2. Isomer Differentiation5.2.1. Isomeric Ions
- 5.2.2. Structural Isomers
- 5.2.3. Positional Isomers
- 5.2.4. Diastereomers
- 5.3. Highly Selective Trace Organic Analysis5.3.1. Chemical Warfare Simulants
- 5.3.2. Explosives
- 5.4. Atmospheric Pressure Eberlin Reactions
- 6. Conclusions
- 7. Acknowledgments
- 8. References
Citing Articles
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This article has been cited by 2 ACS Journal articles (2 most recent appear below).
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O Acylium IonMario Benassi, Luiz Alberto B. Moraes, Liliane G. Cabrini, Luiz Carlos Dias, Andrea M. Aguilar, Gilberto A. Romeiro, Livia S. Eberlin and Marcos N. EberlinThe Journal of Organic Chemistry2008 73 (14), 5549-5557Recognition of Cyclic, Acyclic, Exocyclic, and Spiro Acetals via Structurally Diagnostic Ion/Molecule Reactions with the (CH3)2N-C+
O Acylium IonMario Benassi, Luiz Alberto B. Moraes, Liliane G. Cabrini, Luiz Carlos Dias, Andrea M. Aguilar, Gilberto A. Romeiro, Livia S. Eberlin and Marcos N. EberlinThe Journal of Organic Chemistry2008 73 (14), 5549-5557Reactions of the model acylium ion (CH3)2N-C+
O with acyclic, exocyclic, and spiro acetals of the general formula R1O-CR3R4-OR2 were systematically evaluated via pentaquadrupole mass spectrometry. Characteristic intrinsic reactivities were observed for ...
Intrinsic Gas-Phase Reactivity of Ionized 6-(Oxomethylene)cyclohexa-2,4-dienone: Evidence Pointing to Its Neutral α-Oxoketene Counterpart as a Proper Precursor of Various Benzopyran-4-ones and Analogues
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Paulo Sergio de Carvalho, Fabiane M. Nachtigall, Marcos Nogueira Eberlin, and Luiz Alberto Beraldo MoraesThe Journal of Organic Chemistry2007 72 (16), 5986-5993Despite its unique structure and potential use as an important building block in organic synthesis, the title α-oxoketene 1 has been formed mostly under very special conditions as a short-lived species. The reactivity of 1 is, therefore, nearly ...
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History
- Published In Issue January 11, 2006
- Received May 18, 2005
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