Direct Synthesis of Allyl Sulfides from Allyl Alcohols and Thiols

Shwu-Chen Tsay; Lung Ching Lin; Paul A. Furth; Chi C. Shum; Daniel B. King; Sheng Fa Yu; Buh-Luen Chen; Jih Ru Hwu

doi:10.1055/s-1993-25860

Synthesis 1993; 1993(3): 329-334
DOI: 10.1055/s-1993-25860

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Direct Synthesis of Allyl Sulfides from Allyl Alcohols and Thiols

Shwu-Chen Tsay^* , Lung Ching Lin, Paul A. Furth, Chi C. Shum, Daniel B. King, Sheng Fa Yu, Buh-Luen Chen, Jih Ru Hwu

^*Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan 11529, Republic of China

Abstract

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In the presence of boron trifluoride-diethyl ether complex, various allyl alcohols [(-)-myrtenol, geraniol, cinnamyl alcohol, linalool, 1-octen-3-ol, 2-hydroxybenzyl alcohol and bicyclic diols] were reacted with thiophenol, 1-butanethiol, trimethyl(phenylthio)silane or hexamethylsilane in dichloromethane at room temperature to give the corresponding allyl sulfides in good to excellent yields. The mild conditions for this transformation allowed chemoselectivity.

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