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Note | Special issue | Vol 66, No. 1, 2005, pp.535-542
Published online, 22nd July, 2005
DOI: 10.3987/COM-05-S(K)5
Wittig Rearrangement of Ally 2-Thiophenemethyl Ethers: Facile Synthesis of Thiophenemethanol and -ethanol Derivatives

Masayoshi Tsubuki,* Sohichiro Matsuo, and Toshio Honda*

*Institute of Medical Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


Wittig rearrangement of allyl 2-thiophenemethyl ethers was studied. Deprotonation of allyl 2-thiophenemethyl ethers (1a-d) occurred preferentially either the α- or the α’-position, depending on three kinds of BuLi. Thiophenemethanol and -ethanol derivatives were obtained as products of [2,3] and [1,2] sigmatropic rearrangements, respectively.