213327-64-1Relevant academic research and scientific papers
Allenols versus Allenones: Rhodium-Catalyzed Regiodivergent and Tunable Allene Reactivity with Triazoles
Alcaide, Benito,Almendros, Pedro,Cembellín, Sara,Martínez del Campo, Teresa,Palop, Guillermo
, p. 13754 - 13759 (2017)
2-Pyrrolines and 6-oxo-hexa-2,4-dienals have been prepared through the divergent reactions of 1-benzenesulfonyl-4-aryl-1,2,3-triazoles with functionalized allenes. The rhodium-catalyzed reactions between allenols and 1-benzenesulfonyl-4-aryl-1,2,3-triazoles yielded 2-pyrrolines. This transformation is compatible with the presence of aliphatic, aromatic, heterocyclic, amide, and halogen functional groups. Interestingly, a reactivity switch took place when the allene-tethered alcohol substrate was replaced by its ketone counterpart. When the rhodium-catalyzed reaction of 1-benzenesulfonyl-4-phenyl-1,2,3-triazole was performed with allenones, acyclic 6-oxo-hexa-2,4-dienals were stereoselectively formed as (2Z,4E) isomers.
Studies on the Himbert intramolecular arene/allene diels-alder cycloaddition. Mechanistic studies and expansion of scope to all-carbon tethers
Schmidt, Yvonne,Lam, Jonathan K.,Pham, Hung V.,Houk,Vanderwal, Christopher D.
supporting information, p. 7339 - 7348 (2013/06/27)
The unusual intramolecular arene/allene cycloaddition described 30 years ago by Himbert permits rapid access to strained polycyclic compounds that offer great potential for the synthesis of complex scaffolds. To more fully understand the mechanism of this
A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic, and tetrapropargylic stannanes to carbonyl compounds
McCluskey,Muderawan,Muntari,Young
, p. 7811 - 7817 (2007/10/03)
Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)-tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.
Solvent assisted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to aldehydes and acetals
McCluskey, Adam,Muderawari, I. Wayan,Muntari,Young, David J.
, p. 909 - 911 (2007/10/03)
Tetraallylic, tetraallenic and tetrapropargylic stannanes (0.25 eq) react with aldehydes in methanol to provide unsaturated alcohols. These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)tin 5e and predominantly with allylic rearrangement for tetrapropadienyltin Sc and tetra(2-butynyl)tin 6e. The corresponding TFA catalysed reactions of dimethyl acetals with Sc and 6e are highly regioselective with allylic rearrangement.
