Formal gas-phase polar [4 + 1+] cycloaddition of ionized methylene to alpha-dicarbonyl compounds: synthesis of 2-unsubstituted 1,3-dioxoles |
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Authors: | Meurer Eduardo C Cabrini Liliane G Gozzo Fabio C Eberlin Marcos N |
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Institution: | ThoMSon Mass Spectrometry Laboratory, Institute of Chemistry, State University of Campinas, 13084-971 Campinas SP, Brazil. |
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Abstract: | Ion/molecule reactions of +CH2OCH2. with alpha-dicarbonyl compounds were performed via pentaquadrupole mass spectrometry. Besides the previously known 3+ + 2] 1,3-cycloaddition reaction that forms cyclic 1,3-dioxonium ions, an unprecedented reaction proceeding formally by 4 + 1+] cycloaddition of ionized methylene (CH2+.) to the alpha-dicarbonyl compounds occurs competitively, leading to the gas-phase synthesis of several ionized 2-unsubstituted 1,3-dioxoles. This novel cycloaddition reaction may therefore be added to the set of methods available for the synthesis of 1,3-dioxoles. |
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Keywords: | 1 3‐dioxoles ion/molecule reactions gas‐phase synthesis distonic ions α‐dicarbonyl compounds pentaquadrupole mass spectrometry |
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