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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 20
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Original Articles

Conjugate Addition of Triallylaluminum to α,β‐Unsaturated Nitroalkenes to Produce 4,5‐Unsaturated Nitroalkenes

, , &
Pages 3677-3687 | Received 12 Mar 2006, Published online: 05 Oct 2007
 

Abstract

The reaction of aryl substituted α,β‐unsaturated nitroalkenes 1ag with triallylaluminum 2 in ether solution at 0°C generated low to high yields of 4,5‐unsaturated nitroalkenes 3ag after adding the nitronate to an ice‐cold solution of dilute hydrobromic acid. The yields of products 3hj were increased substantially when the alkyl substituted α,β‐unsaturated nitroalkene 1h and the highly hindered α,β‐unsaturated nitroalkenes 1i and 1j reacted with 2 in the presence of aluminum chloride. The most important thing is triallylaluminum was prepared from allyl bromide and pure elemental Al, not from Grignard reagent.

Acknowledgments

Financial support by National Taiwan Normal University ORD 93‐C and National Science Council of the Republic of China is gratefully acknowledged. We also thank Professor Milton S. Feather for helpful discussions during the preparation of the manuscript.

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