Reactions of carbanions with 2,4-dinitrofluorobenzene leading to stable heptatrienide moieties

Autor:	Zoija A. Starikova, Yuri G. Gololobov, Pavel V. Petrovskii, I. A. Garbuzova, Olesya A. Linchenko
Rok vydání:	2007
Předmět:	chemistry.chemical_compound Dinitrofluorobenzene Chemistry Stereochemistry Zwitterion Heteroatom Alkoxy group Moiety General Chemistry Conjugated system Decomposition Medicinal chemistry Carbanion
Zdroj:	Heteroatom Chemistry. 18:108-115
ISSN:	1098-1071 1042-7163
DOI:	10.1002/hc.20267
Popis:	Reactions of NCCH2COOMe 1a and CH2(CN)21b with 2,4-dinitrofluorobenzene 2 at the presence of Et3 N result in deeply colored crystalline stable salts 4a,4b with anions that contain a system of conjugated bonds. Similar reaction of 2 with phosphorus-containing zwitterion 6 bearing ethoxy- and cyano-groups at the carbanion center is the first example of the reaction leading to the formation of P-zwitterion 9 with a negatively charged heptatriene moiety. This reaction proceeds via a new route of decomposition of the intermediate σ-complex 7 occurring with formation of ethylfluoroformate. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:108–115, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20267
Databáze:	OpenAIRE
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