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

✍ Scribed by Yuri G. Gololobov; Olesya A. Linchenko; Pavel V. Petrovskii; Zoija A. Starikova; Irina A. Garbuzova

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
238 KB
Volume
18
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Reactions of NCCH~2~COOMe 1a and CH~2~(CN)~2~ 1b with 2,4‐dinitrofluorobenzene 2 at the presence of Et~3~ 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

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New reaction of pyridinium ylide with 2,
New reaction of pyridinium ylide with 2,4,6-trinitrofluorobenzene leading to stable heptatrienide moiety
✍ Yuri G. Gololobov; Olesya A. Linchenko; Pavel V. Petrovskii; Victor N. Khrustale 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 English ⚖ 195 KB 👁 1 views

## Abstract A new reaction of pyridinium ylide (**4**) with 2,4,6‐trinitrofluorobenzene leading to stable negatively charged heptatriene moiety (**6**) is described. This reaction proceeds via a new route of decomposition of intermediate σ‐complex (**5**) occurring with the formation of ethylfluoro