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A New and Efficient Synthesis of Highly Functionalized (Triphenylphosphoranylidene)cyclopentadienes with Zwitterionic Resonance Structures

✍ Scribed by Abdolali Alizadeh

Publisher: John Wiley and Sons
Year: 2005
Tongue: German
Weight: 68 KB
Volume: 88
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200590012

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✦ Synopsis

Different esters of 2-aryl-4-hydroxy-3-nitro-5-(triphenylphosphoranylidene)cyclopenta-1,3-diene-1-carboxylates 1 were prepared in excellent yields from the 1 : 1 : 1 reaction between Ph 3 P, dialkyl acetylenedicarboxylates 2, and (substituted) 2-(nitroethenyl)benzenes 3 (Scheme 1). The structures of the highly functionalized compounds 1 were corroborated spectroscopically (IR, 1 H-, 13 C-, 31 P-NMR, EI-MS) and by elemental analyses. A plausible mechanism for this type of cyclization is proposed (Scheme 2).

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