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Synthesis of Bis‐spiro Cyclopropanes Based on Meldrum’s Acid by Milling
Author(s) -
Kashani Elmira,
Noroozi Pesyan Nader,
Tunç Tuncay,
Sahin Ertan
Publication year - 2015
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201400320
Subject(s) - chemistry , sodium ethoxide , meldrum's acid , cyanogen bromide , solvent , bromide , proton nmr , nuclear magnetic resonance spectroscopy , organic chemistry , ethanol , biochemistry , peptide sequence , gene
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 1 H NMR, 13 C 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.