Probing the mechanism of the Petasis olefination reaction by atmospheric pressure chemical ionization mass and tandem mass spectrometry |
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| Authors: | Meurer Eduardo Cesar Santos Leonardo Silva Pilli Ronaldo Aloise Eberlin Marcos N |
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| Affiliation: | Institute of Chemistry, State University of Campinas-UNICAMP, 13083-970 Campinas, SP, Brazil. |
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| Abstract: | Atmospheric pressure chemical ionization mass (APCI-MS) and tandem mass spectrometry (APCI-MS/MS) is used to probe the mechanism of the Petasis olefination reaction. Oxatitanacycle intermediates 4 were transferred from solution to the gas phase, detected as 4H+ by APCI-MS with characteristic Ti-isotopic patterns, and structurally characterized by APCI-MS/MS. Detection of 4H+, which upon collision activation dissociates to both 3H+ and Cp(2)TiOH+, fully supports the Hughes mechanism as depicted above. [reaction: see text] |
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