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

Alizadeh Abdolali | Zendy

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

Author(s) -

Alizadeh Abdolali

Publication year - 2005

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200590012

Subject(s) - chemistry , aryl , nitro , resonance (particle physics) , medicinal chemistry , carbon 13 nmr , diene , proton nmr , stereochemistry , combinatorial chemistry , organic chemistry , alkyl , physics , natural rubber , particle physics

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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