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Volumn 10, Issue 25, 2012, Pages 4847-4850

Precipitation-driven self-sorting of imines

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES;

AROMATIC ALDEHYDE; SELF-SORTING; SOLVENT MIXTURES; SUBSTITUTED ANILINES;

NITROGEN COMPOUNDS;

EID: 84862227286 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c2ob25736j Document Type: Article

Times cited : (29)

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- Yields of individual imines were calculated from the overall mass recovery of the mixture and ¹H NMR spectra integration data. Isolation of individual imines would have likely altered the distribution of the products and was not performed When H2O was slowly added to this diluted mixture of imines, slow and incomplete precipitation occurred, yielding mixtures of imines in both the precipitate and the mother liquor Imine mixtures precipitated from EtOH-H2O exhibit a certain degree of kinetic stability after re-dissolution in MeCN: mixture obtained in experiment shown in Scheme 2 (bottom) did not change in composition even after 7 days in MeCN solution at 25 °C. Equilibration into the random mixture of products was achieved only after heating in MeCN at reflux for 24 h. This kinetic stability is perhaps unsurprising, as rapid imine exchange often requires catalysis by free anilines. See, for example
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