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Acta Chimica Sinica ›› 2006, Vol. 64 ›› Issue (21): 2190-2196. Previous Articles Next Articles
Original Articles
安德烈*, 孟桂英, 张志扬, 张留成, 张英俊, 陈强, 严宏
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AN De-Lie*; MENG Gui-Ying; ZHANG Zhi-Yang; ZHANG Liu-Cheng; ZHANG Ying-Jun; CHEN Qiang; YAN Hong
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A novel method for synthesis of methylthio aryl ethynes was described, and eight compounds 1a~1h were obtained by the one-pot protocol starting from methylthiomethyl phenyl sulfone (MP-S) and aromatic aldehydes. The mechanism for the formation of 1 was discussed on the basis of trapping and characterization of some important intermediates. The results from experiments indicated that the reaction might involve the initial nucleophilic addition of MP-S to aromatic aldehyde to produce an intermediate 2 carrying two leaving groups, followed by double eliminations using lithium diisopropylamide (LDA) as base to form 1. This method is not only simple, but also does not require a tedious separation of the reaction mixtures because of less by-product.
Key words: double elimination, one-pot synthesis, methylthio aryl ethyne, methylthiomethyl phenyl sulfone, aromatic aldehyde
AN De-Lie*; MENG Gui-Ying; ZHANG Zhi-Yang; ZHANG Liu-Cheng; ZHANG Ying-Jun; CHEN Qiang; YAN Hong. One-Pot Synthesis of Methylthio Aryl Ethynes by Double Elimination Protocol[J]. Acta Chimica Sinica, 2006, 64(21): 2190-2196.
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