15564-30-4Relevant articles and documents
Halogen-Substituted Allenyl Ketones through Ring Opening of Nonstrained Cycloalkanols
Wu, Penglin,Ma, Shengming
supporting information, p. 2533 - 2537 (2021/04/13)
An efficient synthesis of halogen-substituted allenyl ketones via Ag-catalyzed oxidative ring opening of allenyl cyclic alcohols under mild reaction conditions has been achieved. The reaction features a wide substrate scope and excellent regioselectivity. The synthetic potential of the products has been demonstrated by their conversion to stereodefined alkenes and heterocyclic compounds.
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.
