83520-80-3Relevant 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.
Synthesis and olfactory evaluation of bulky moiety-modified analogues to the sandalwood odorant polysantol
Chapado, Laura,Linares-Palomino, Pablo J.,Badia, Concepcion,Salido, Sofia,Nogueras, Manuel,Sanchez, Adolfo,Altarejos, Joaquin
experimental part, p. 2780 - 2800 (2010/03/24)
Five new bulky moiety-modified analogues of the sandalwood odorant Polysantol have been synthesized by aldol condensation of appropriate aldehydes with butanone, deconjugative α-methylation of the resulting α,β-unsaturated ketones, and reduction of the co
Carbon-carbon bond forming reactions of η3-allyl iron tricarbonyl anions with carbon electrophiles
Chang, Seok,Yoon, Jaeyon,Brookbart, Maurice
, p. 1869 - 1879 (2007/10/02)
Reaction of the η3-allyl iron tricarbonyl anion, 1, with alkyl halides (RX, R = -CH3, -CH2Ph, -(CH2)3CH3, -CH(CH3)2,-CH2CH=CH2) followed by treat
Deshydratation des diols-1,2α,β-ethyleniques IV: role de la stereomutation des carbocations allyliques α-hydroxyles sur l'orientation des reactions observees
Dana, Gilbert,Gharbi-Benarous, Josyane,Thuan, Sa Le Thi
, p. 1451 - 1462 (2007/10/02)
The allylic carbocations formed during the dehydration of diols of type A are found to react by five different processes: three nucleophilic attacks (by solvent at the β or δ positions, or by the intramolecular hydroxyl group at δ), a degradation reaction between Cα and Cβ and the classical pinacol rearrangement.Nucleophilic attack at the carbon δ is a very efficient reaction and sometimes (for monosubstituted substrates in β, γ or δ) gives quasi-exclusive products: a ketone for the reaction with H2O in δ or a 2,5-dihydrofuran product for the intramolecular reaction.In the case of γ and δ disubstituted carbocations, the selectivity is less and we show that it is possible to analyze the different steric effects commanding the stereomutation equilibrium of the allylic carbocation and so determining the orientation in the dehydration.
