Reactions of 1,3-diaryl-2-chloropropane-1,3-diones with nucleophiles - Cyanide-induced retro-Claisen-Claisen condensation Full article
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European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690 |
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| Output data | Year: 2004, Number: 8, Pages: 1765-1773 Pages count : 9 DOI: 10.1002/ejoc.200300739 | ||||
| Tags | Diaroylmethanes; Enaminones; Ketones; Nucleophilic substitution; Retro-Claisen-Claisen condensation | ||||
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Abstract:
Treatment of some 1,3-diaryl-2-chloropropane-1,3-diones, acyclic chloro-substituted enaminones and β-oxo esters with nucleophiles was shown to proceed easily with the formation, at least in the first stage, of formal nucleophilic substitution products. Treatment of enaminones and β-oxo esters with azide and cyanide ions proceeds with the preservation of the skeleton, whereas chloro-substituted diaroylmethanes undergo retro-Claisen-Claisen condensation reactions in the course of the reaction with cyanide. Dibenzoylchloromethane reacts with azide and cyanide ions with fragmentation of the molecule and subsequent reassembly, resulting in benzoylated benzaldehyde cyanohydrin and a 1,3-oxathiol derivative, respectively. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Cite:
Roshchupkina G.I.
, Gatilov Y.V.
, Rybalova T.V.
, Reznikov V.A.
Reactions of 1,3-diaryl-2-chloropropane-1,3-diones with nucleophiles - Cyanide-induced retro-Claisen-Claisen condensation
European Journal of Organic Chemistry. 2004. N8. P.1765-1773. DOI: 10.1002/ejoc.200300739 WOS Scopus РИНЦ OpenAlex
Reactions of 1,3-diaryl-2-chloropropane-1,3-diones with nucleophiles - Cyanide-induced retro-Claisen-Claisen condensation
European Journal of Organic Chemistry. 2004. N8. P.1765-1773. DOI: 10.1002/ejoc.200300739 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Apr 1, 2004 |
Identifiers:
| Web of science: | WOS:000221027500014 |
| Scopus: | 2-s2.0-4544219752 |
| Elibrary: | 13463167 |
| OpenAlex: | W2031765874 |