Formal gas-phase polar [4 + 1+] cycloaddition of ionized methylene to α-dicarbonyl compounds: synthesis of 2-unsubstituted 1,3-dioxoles
✍ Scribed by Eduardo C. Meurer; Liliane G. Cabrini; Fabio C. Gozzo; Marcos N. Eberlin
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 145 KB
- Volume
- 41
- Category
- Article
- ISSN
- 1076-5174
- DOI
- 10.1002/jms.1029
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✦ Synopsis
Abstract
Ion/molecule reactions of ^+^CH~2~ OCH~2~^·^ with α‐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 (CH~2~^+·^) to the α‐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. Copyright © 2006 John Wiley & Sons, Ltd.