In Pursuit of an Acetylenedithiolate Synthesis
In Pursuit of an Acetylenedithiolate Synthesis
复制标题
乙炔二硫醇盐的合成
DOI：
10.1002/ejoc.200601107
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发表时间：
2007
影响因子：
2.8
通讯作者：
T. Pape
中科院分区：
文献类型：
--
作者：
W. Seidel;Matthias J. Meel;M. Schaffrath;T. Pape
Acetylene disulfides RSC2SR, which are furnished with typical thiol protection groups R, were synthesized, fully characterized, and tested with respect to the aimed cleavage of R. While the alkyne RSC2SR with R = C2H4SiMe3 is easily accessible, the corresponding disulfide with R = CPh3 can be prepared only with difficulties, and attempts to use the SiMe3 group lead to the isolation of a dithiacyclopentene derivative. The molecular structures of Ph3CSC2SCPh3 and Ph3CSC2H, which were investigated by X-ray diffraction, show a remarkable combination of long and very short carbon–sulfur single bonds. However, removal of the trityl groups by sodium phenolate or methyllithium in THF led to intractable solutions. In contrast, removal of both trimethylsilylethyl groups in Me3SiC2H4SC2SC2H4SiMe3 with (Bu4N)F in THF proceeded smoothly, if benzyl bromide as the trapping agent is present. Hence, the successful transfer of the C2S22– synthon in solution was proven by isolation of BnSC2SBn.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
