Simpkins Simon M E, Kariuki Benson M, Aricó Caterina S, Cox Liam R
School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.
Org Lett. 2003 Oct 16;5(21):3971-4. doi: 10.1021/ol035536e.
[reaction: see text] A highly regio- and stereoselective bis-stannylation of unsymmetrically substituted butadiyne 3 provides bis-stannane 4. Selective lithiation of the internal tin residue effects a 1,4-retro-Brook rearrangement to afford vinylsilane 5. This was elaborated into the novel diethynylethene 1, which also functions as a masked triyne.
[反应：见正文] 对不对称取代的丁二炔3进行高度区域和立体选择性的双锡基化反应，得到双锡烷4。内部锡残基的选择性锂化作用引发1,4-逆布鲁克重排，得到乙烯基硅烷5。将其进一步转化为新型二乙炔基乙烯1，它也可作为掩蔽的三炔起作用。
