Issue 19, 1993
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

[3 + 2]-Annulation using allylidene(triphenyl)phosphoranes: a one-step synthesis of cyclopentadienes

Minoru Hatanaka,   Yuichiro Himeda  and  Ikuo Ueda  

Abstract

A convenient method for the synthesis of substituted cyclopentadienes has been developed using allylidene(triphenyl)phosphoranes. (3-Ethoxycarbonyl-2-substituted-2-propenylidene)triphenylphosphoranes 1 reacted with α-halogenoketones under very mild reaction conditions to undergo a [3 + 2]-annulation leading to the regioselective formation of tri- or tetra-substituted cyclopentadienes in good to excellent yields. Allylidenephosphoranes 1 also reacted with S-ethyl bromoethanethioate to yield 4-ethylthiocyclopentadienes, which was readily converted into a cyclopentenone.

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Article information

DOI
https://doi.org/10.1039/P19930002269
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 2269-2274

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[3 + 2]-Annulation using allylidene(triphenyl)phosphoranes: a one-step synthesis of cyclopentadienes

M. Hatanaka, Y. Himeda and I. Ueda, J. Chem. Soc., Perkin Trans. 1, 1993, 2269 DOI: 10.1039/P19930002269

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