Synthesis of Bis-spiro Cyclopropanes Based on Meldrum's Acid by Milling

Reaction of 2,2‐dimethyl‐1,3‐dioxane‐4,6‐dione (Meldrum’s acid) with various solid aldehydes in the presence of cyanogen bromide and solid sodium ethoxide (EtONa) leads to the selective and efficient formation of bis‐spiro cyclopropanes based on Meldrum’s acid at the range of 0 °C to room temperatur...

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Bibliographic Details
Published in:Journal of the Chinese Chemical Society (Taipei) 2015-03, Vol.62 (3), p.249-256
Main Authors: Kashani, Elmira, Noroozi Pesyan, Nader, Tunç, Tuncay, Sahin, Ertan
Format: Article
Language:English
Subjects:
Aldehyde
Bis-spiro cyclopropanes
Cyanogen bromide
Meldrum's acid
Milling
Solid sodium ethoxide
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Summary:Reaction of 2,2‐dimethyl‐1,3‐dioxane‐4,6‐dione (Meldrum’s acid) with various solid aldehydes in the presence of cyanogen bromide and solid sodium ethoxide (EtONa) leads to the selective and efficient formation of bis‐spiro cyclopropanes based on Meldrum’s acid at the range of 0 °C to room temperature. The products were obtained in good to excellent yields. Structure elucidation is carried out by 1H NMR, 13C NMR, FT‐IR spectroscopy, mass analyses and X‐ray crystallography techniques. A possible mechanism for the formation of products is also discussed under solvent‐free condition. Reaction of Meldrum’s acid with various solid aldehydes in the presence of cyanogen bromide and solid sodium ethoxide leads to the selective and efficient formation of bis‐spiro cyclopropanes based on Meldrum’s acid at the range of 0 °C to room temperature by milling.
ISSN:0009-4536
2192-6549
DOI:10.1002/jccs.201400320