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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 12
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Original Articles

Facile Synthesis of 4‐Functionalized Cyclopentenones

Sujit Kumar Ghorai Department of Chemistry, Indian Institute of Technology, Kharagpur, India
,
Nirmal Kumar Hazra Department of Chemistry, Indian Institute of Technology, Kharagpur, India
&
Dipakranjan Mal Department of Chemistry, Indian Institute of Technology, Kharagpur, IndiaCorrespondence[email protected]
Pages 1949-1956 | Received 26 Oct 2006, Published online: 22 Jun 2007
 
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Abstract

1-8-Diazabicyclo[5.4.0]undec-7-ene(DBU)‐catalyzed Michael addition of nitroalkanes to dicyclopentadienone (1) followed by flash vacuum pyrolysis (FVP) provided a high‐yielding synthesis of extremely pure 4‐nitroalkyl cyclopentenones (3). The optimized Nef reaction of the nitro adducts (2) provided 4‐ketoalkyl cyclopentenones (5) in the similar way.

Acknowledgment

Financial assistance for this work from the Department of Science and Technology (DST) and the Council of Scientific and Industrial Research (CSIR), New Delhi, is gratefully acknowledged.

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