55980-52-4Relevant academic research and scientific papers
Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); A new 'metal free' life for the Rupe rearrangement
Nandi, Ganesh C.,Rathman, Benjamin M.,Laali, Kenneth K.
supporting information, p. 6258 - 6263 (2013/10/22)
A mild and selective transition metal free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Br?nsted acidic ionic liquid [BMIM-SO3H][OTf] as catalyst and [BMIM][PF 6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov sequence utilizing this protocol has also been demonstrated.
Efficient routes to cyclic 2,3-epoxyalcohols from cycloalkenyl ketones, via cycloalkenyl alcohols
Marson,Walker,Pickering,Harper,Wrigglesworth,Edge
, p. 10317 - 10338 (2007/10/02)
The minimising of torsional strain and non-bonding interactions is proposed as the explanation of high diastereoselectivity observed in the epoxidation of cycloalkenyl alcohols, reported for twenty three examples. The resulting 2,3-epoxyalcohols are key i
Vinyl Cations, 37. Rearrangement of Cyclic Homopropargyl Sulfonates to Condensed Cyclobutanones and Cyclopropyl Ketones
Hanack, Michael,Schuhmacher, Werner,Kunzmann, Erich
, p. 1467 - 1487 (2007/10/02)
Cyclic homopropargyl sulfonates 8 (tosylates, triflates, nonaflates, and damsylates) are prepared and solvolysed.The resulting rearrangement reactions are studied with respect to the properties of the solvents used, leaving groups, the substituent on the triple bond, and with respect to the ring size of the sulfonates 8.
