326496-12-2Relevant academic research and scientific papers
Ortho-[2,3]-wittig rearrangement of benzyl propargyl ethers: Striking preference over the competing [1,2]-wittig shift
Tomooka, Katsuhiko,Harada, Manabu,Hanji, Takayuki,Nakai, Takeshi
, p. 1394 - 1395 (2000)
Treatment of benzyl γ-(trimethylsilyl)propargyl ether with n-BuLi is shown to afford the rarely precedent ortho-[2,3]-Wittig product in remarkable preference to the [1,2]-Wittig product. The factors governing the periselectivity in this type of carbanion
Fluoride-assisted activation of calcium carbide: A simple method for the ethynylation of aldehydes and ketones
Hosseini, Abolfazl,Seidel, Daniel,Miska, Andreas,Schreiner, Peter R.
supporting information, p. 2808 - 2811 (2015/06/16)
The fluoride-assisted ethynylation of ketones and aldehydes is described using commercially available calcium carbide with typically 5 mol % of TBAF·3H2O as the catalyst in DMSO. Activation of calcium carbide by fluoride is thought to generate an acetylide "ate"-complex that readily adds to carbonyl groups. Aliphatic aldehydes and ketones generally provide high yields, whereas aromatic carbonyls afford propargylic alcohols with moderate to good yields. The use of calcium carbide as a safe acetylide ion source along with economic amounts of TBAF·3H2O make this procedure a cheap and operationally simple method for the preparation of propargylic alcohols.
Synthesis of acetylenic alcohols with calcium carbide as the acetylene source
Sum, Yin Ngai,Yu, Dingyi,Zhang, Yugen
supporting information, p. 2718 - 2721 (2013/10/08)
Propargyl alcohols containing a terminal alkyne group are highly important and versatile intermediates. Here, we report the synthesis of these compounds from an inexpensive and renewable resource, calcium carbide (CaC2). No metal catalysts are required in this new protocol and the reactions take place under very mild conditions.
