Ortho versus α-Metalation of Ethyl Phenyl Sulfide by n-Butyllithium/N, N, N', N'-Tetramethylethylenediamine: Synthesis, Reactivity, and Crystal Structures of (2-( …

…, C Bruhn, T Rüffer, H Schmidt, D Steinborn

文献索引：Linnert, Matthias; Bruhn, Clemens; Rueffer, Tobias; Schmidt, Harry; Steinborn, Dirk Organometallics, 2004 , vol. 23, # 15 p. 3668 - 3673

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被引用次数: 16

摘要

Metalation of ethyl phenyl sulfide by n-BuLi/tmeda (tmeda= N, N, N', N''- tetramethylethylenediamine) is strongly solvent dependent: In n-hexane and diethyl ether ortho lithiation occurred, yielding 1, while in THF α-lithiation occurred, yielding 2. Dissolution of 1 in tetrahydrofuran resulted in isomerization, forming quantitatively the α-lithiated compound 2. X-ray structure analyses showed that 1 and 2 are dimeric in the solid state, ...