New mechanistic approaches the reaction Morita-Baylis-Hillman (AZA, classical and asymmetric) by mass spectrometry

• Grant number: 12/10701-3
• Support Opportunities: Scholarships in Brazil - Master
• Effective date (Start): October 01, 2012
• Effective date (End): September 30, 2014
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Marcos Nogueira Eberlin
• Grantee: Renan de Souza Galaverna
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

The reaction mechanisms can be proposed based on the reactivity of chemical compounds involved. In the past, these proposals were supported (or discredited), primarily through the isolation of the intermediates or on the basis of spectroscopic and kinetic data. Moreover, the difficulty of detecting transient species in solution hindered the consolidation and elucidation of these mechanisms.The understanding of mechanisms that operate in such chemical processes arouses the fascination of synthetic organic chemists, and a constant challenge in this area.Therefore, this research project we are proposing to carry out a detailed mechanistic investigation of the three versions of Morita-Bayllis-Hillman (MBH-classical, aza and asymmetric), using the technique of mass spectrometry ESI-MS/MS in order to clarify and strengthen proposals currently suggested in the literature. A new approach is used for the MBH-aza versions, classic reagents which are marked with loads (Charged tags), which facilitate the detection and carry more information for analysis by mass spectrometry. Moreover, a study of the asymmetric version of classical MBH catalyzed by a chiral amines also be addressed. In this case, experiments will be performed for the separation of stereoisomers possible mechanism using formed during the ion mobility (Twim-MS). (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

GALAVERNA, RENAN S.; BATAGLION, GIOVANA A.; HEERDT, GABRIEL; DE SA, GILBERTO F.; DARODA, ROMEU; CUNHA, VALNEI S.; MORGON, NELSON H.; EBERLIN, MARCOS N.. Are Benzoic Acids Always More Acidic Than Phenols? The Case of ortho-, meta-, and para-Hydroxybenzoic Acids. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, n. 10, p. 2189-2196, APR 2015. (12/10701-3, 12/21395-0)

GALAVERNA, RENAN; CAMILO, NILTON S.; GODOI, MARLA N.; COELHO, FERNANDO; EBERLIN, MARCOS N.. Charge Tags for Most Comprehensive ESI-MS Monitoring of Morita-Baylis-Hillman (MBH)/aza-MBH Reactions: Solid Mechanistic View and the Dualistic Role of the Charge Tagged Acrylate. Journal of Organic Chemistry, v. 81, n. 3, p. 1089-1098, FEB 5 2016. (13/10449-5, 12/10701-3)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

GALAVERNA, Renan de Souza. s-Hillman reaction (aza, classic and asymmetric) by mass spectrometry. 2014. Master's Dissertation - Universidade Estadual de Campinas (UNICAMP). Instituto de Química Campinas, SP.