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Novel Synthesis of Alkenes via Triethylborane-Induced Free-Radical Reactions of Alkyl Iodides and β-Nitrostyrenes

Ju-Tsung Liu, Yeong-Jiunn Jang, Yuh-Kuo Shih, Shin-Ru Hu, Cheng-Ming Chu and Ching-Fa Yao*

*Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei, Taiwan 116, Republic of China, Email:

J.-T. Liu, Y.-J. Jang, Y.-K. Shih, S.-R. Hu, C.-M. Chu, C.-F. Yao, J. Org. Chem., 2001, 66, 6021-6028.

DOI: 10.1021/jo010213m

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Reactions of (E)-β-nitrostyrenes with triethylborane or tricyclohexylborane in THF solution at room temperature in the presence of oxygen in the air as radical initiator generate high yields of trans-alkenes. (E)-alkenes can also be prepared when (E)-β-nitrostyrenes react with different radicals, prepared from secondary or tertiary alkyl iodides in the presence of triethylborane and air.

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proposed mechanism

Key Words


ID: J42-Y2001