An Efficient Synthesis of Stable Phosphorus Ylides Derived from Pyrazole and Indazole

Stable crystalline phosphorus ylides were obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, in the presence of strong NH-acids, such as pyrazole, indazole and 5-nitro Indazole. These stable ylides exist in solution as a mixt...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2006-01, Vol.181 (1), p.25-30
Main Authors: Maghsoodlou, Malek Taher, Hazeri, Nourollah, Khorasani, Sayyed Mostafa Habibi, Kakaei, Reza, Nassiri, Mahmoud
Format: Article
Language:English
Subjects:
Acetylenic ester
NH-acid
stable phosphorus ylides
triphenylphosphine
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Summary:Stable crystalline phosphorus ylides were obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, in the presence of strong NH-acids, such as pyrazole, indazole and 5-nitro Indazole. These stable ylides exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group.
ISSN:1042-6507
1563-5325
DOI:10.1080/104265090968479