55103-82-7Relevant academic research and scientific papers
Traceless Isoprenylation of Aldehydes via N-Boc-N-(1,1-dimethylallyl)hydrazones
Heerdegen, Desirée,Junker, Julia,Dittrich, Sebastian,Mayer, Peter,Bracher, Franz
, p. 3680 - 3687 (2020/06/02)
A short isoprenylation protocol starting from non-conjugated N-Boc-N-(1,1-dimethylallyl)hydrazones was developed utilising Thomson's traceless bond construction. This type of [3,3]-sigmatropic rearrangement is catalysed by the Br?nsted acid triflimide and liberates only gaseous by-products. The required N-Boc-N-allylhydrazine precursor is available in three steps starting from a known diazene using biocatalytic aldol addition and Tebbe olefination as key steps. Allylhydrazones are prepared via condensation with appropriate aldehydes. Scope and limitations of the [3,3]-sigmatropic rearrangements are analysed.
Amberlyst-15: A reusable heterogeneous catalyst for the dehydration of tertiary alcohols
Frija, Luís M.T.,Afonso, Carlos A.M.
experimental part, p. 7414 - 7421 (2012/09/22)
Tertiary alcohols react under mild conditions in the presence of Amberlyst-15 (dry) (solid-supported sulfonic acid) to give predominantly the most stable alkene in very good yield. The dehydration of tertiary alcohol functionality occurs without observation of rearrangement and polymerization products, and with outstanding substrate tolerance, which include the NHCBz, NHBoc, OSEM, OTBDMS, OBOM and ethylene ketal functional groups. Amberlyst-15 (dry) can be easily recovered from the reaction medium and reused for five cycles, maintaining the catalytic efficiency. In addition, the dehydration can occur under continuous operation.
3,5-Bis(trifluoromethyl)phenyl sulfones in the Julia-Kocienski olefination - Application to the synthesis of tri- and tetrasubstituted olefins
Alonso, Diego A.,Fuensanta, Monica,Najera, Carmen
, p. 4747 - 4754 (2007/10/03)
3,5-Bis(trifluoromethyl)phenyl (BTFP) sulfones 8a-d are successfully employed in the modified Julia olefination reaction with carbonyl compounds employing phosphazene base P4-tBu at room temp. in THF, affording tri- and tetrasubstituted olefins in good yi
Nitrous oxide oxidation catalyzed by ruthenium porphyrin complex
Tanaka, Hirotaka,Hashimoto, Kentaro,Suzuki, Kyosuke,Kitaichi, Yasunori,Sato, Mitsuo,Ikeno, Taketo,Yamada, Tohru
, p. 1905 - 1914 (2007/10/03)
Dinitrogen oxide was employed as a clean oxidant for various oxidations in the presence of a catalytic amount of dioxoruthenium tetramesitylporphyrin complex (Ru(tmp)(O)2). A variety of olefins, secondary alcohols, and benzyl alcohols were smoothly oxidized to the corresponding epoxides, ketones, and aldehydes in high yields. In the oxidation of 9,10-dihydroanthracene derivatives, the competitive reactions affording anthraquinones and anthracenes could be regulated by the reaction conditions. At a high temperature (200°C), anthraquinones were selectively produced, while the anthracenes were selectively produced by the addition of sulfuric acid.
Conversion of non-activated alkenes into cyclopropanes with lithiated sulfones under nickel catalysis
Gai, Yonghua,Julia, Marc,Verpeaux, Jean-Noel
, p. 817 - 829 (2007/10/03)
Summary -Lithiated alkyl ierf-butyl sulfones convert alkenes into cyclopropane derivatives under nickel catalysis. The new reaction appears to differ from the known cyclopropanation reactions from both the stereochemical and the electronic points of view. Elsevier.
