27428-33-7Relevant articles and documents
Decarbonylative Olefination of Aldehydes to Alkenes
Ainembabazi, Diana,Reid, Christopher,Chen, Amanda,An, Nan,Kostal, Jakub,Voutchkova-Kostal, Adelina
supporting information, p. 696 - 699 (2020/01/31)
New atom-economical alternatives to Wittig chemistry are needed to construct olefins from carbonyl compounds, but none have been developed to-date. Here we report an atom-economical olefination of carbonyls via aldol-decarbonylative coupling of aldehydes using robust and recyclable supported Pd catalysts, producing only CO and H2O as waste. The reaction affords homocoupling of aliphatic aldehydes, as well as heterocoupling of aliphatic and aromatic ones. Computations provide insight into the selectivity and thermodynamics of the reaction. The tandem aldol-decarbonylation reaction opens the door to exploration of new carbonyl reactivity to construct olefins.
Fluorodecarboxylation, rearrangement and cyclisation: the influence of structure and environment on the reactions of carboxylic acids with xenon difluoride
Ramsden, Christopher A.,Shaw, Maxine M.
experimental part, p. 3321 - 3324 (2009/08/09)
The reactions of structurally diverse carboxylic acids with XeF2 in both CH2Cl2/Pyrex and CH2Cl2/PTFE have been studied. Pyrex appears to be a very effective heterogeneous catalyst for an electrophilic mode of reaction of polarised XeF2, leading to rearrangement, cyclisation and cationic products. In CH2Cl2/PTFE, fluorodecarboxylation is the main mode of reaction, in accordance with previous studies, and may occur via a SET reaction of unpolarised XeF2.
Reaction of Hydrazones with Methoxy(tosyloxy)iodobenzene (MTIB): Tosylate Formation under Oxidative Conditions
Ramsden, Christopher A.,Rose, Helen L.
, p. 27 - 28 (2007/10/03)
Treatment of aromatic hydrazones 1 containing electron-withdrawing, reduction sensitive substituents with MTIB gives the corresponding tosylates 2 in high yield. When the tosylate is particularly reactive the thermodynamically more stable methyl ether 3 is isolated. Analogous reactions with DAIB give acetates 4 in high yield. Dialkyl hydrazones give olefinic products (e.g. 7 and 8). (+)-Camphor hydrazone 1k with either MTIB or DAIB gives both camphene 12 (major product) and tricyclene 11 (minor product) suggesting that a carbene pathway accounts for some of the material formed in these oxidations.
