81149-96-4Relevant academic research and scientific papers
Dehydrogenative Synthesis of Linear α,β-Unsaturated Aldehydes with Oxygen at Room Temperature Enabled by tBuONO
Wang, Mei-Mei,Ning, Xiao-Shan,Qu, Jian-Ping,Kang, Yan-Biao
, p. 4000 - 4003 (2017/06/19)
Synthesis of linear α,β-unsaturated aldehydes via a room-temperature oxidative dehydrogenation has been realized by the cocatalysis of an organic nitrite and palladium with molecular oxygen as the sole clean oxidant. Linear α,β-unsaturated aldehydes could be efficiently prepared under aerobic catalytic conditions directly from the corresponding saturated linear aldehydes. Besides linear products, the aromatic analogy could also be smoothly achieved by the same standard method. The organic nitrite redox cocatalyst and alcohol solvent play a key role for realizing this method.
Beckmann-rearrangement of cyclododecanone oxime to ω-laurolactam in the gas phase
Eickelberg,Hoelderich
experimental part, p. 42 - 55 (2009/06/17)
The classical route for the industrial production of ω-laurolactam is the homogeneously catalyzed Beckmann-rearrangement of cyclododecanone oxime in the liquid state using fuming sulfuric acid catalyst. Contrary to that, a completely different way is shown in the present work. In addition to the use of a solid acid catalyst, the vapor phase was chosen. From a process technical point of view it is a superior route compared with the classical one. Following intensive investigations of the vapor phase behavior of substrate, product and the main by-products, a catalyst screening of the most promising materials was performed. In addition, a modification of the most active catalysts was carried out to get more information about reaction sites and to optimize the catalyst activity. Using an acid treated [Al,B]-BEA zeolite at a temperature of approx. 320 °C and reduced pressures, complete conversion combined with excellent selectivity of 98% were obtained. The accumulation of reactants in the fixed bed was less than 5 wt%. Furthermore, investigations of deactivation and regeneration behavior of the catalyst were done. It could be demonstrated that the catalytic material could be regenerated under oxidative atmosphere as well as under non-oxidative conditions through thermal desorption of the deactivating compounds without any measurable loss of catalytic performance.
Radical addition to (2,3-epoxy-4-pentenyloxy)trialkylsilanes yielding α,β-unsaturated aldehydes via carbon-carbon bond cleavage
Tanaka, Shinobu,Nakamura, Tomoaki,Yorimitsu, Hideki,Oshima, Koichiro
, p. 569 - 572 (2007/10/03)
Treatment of (2,3-epoxy-4-pentenyloxy)trialkylsilane with radical precursors such as triphenylgermane and α-halo carbonyl compounds in the presence of Et3B yields α,β-unsaturated aldehydes. The reaction involves β-scission of a secondary alkoxy radical that releases a siloxymethyl radical.
A simple and inexpensive synthesis of 2-alkenals
Chang,Uang,Wu,Yu
, p. 1033 - 1034 (2007/10/02)
A simple and inexpensive method for the C2 homologation of aldehydes and ketone to 2-alkenals consists of the reaction with allylmagnesium bromide, O-acylation of the resultant 1-alken-4-ol, and ozonolysis.
Cerium or Ruthenium Catalyzed Oxidation of Alcohols to Carbonyl Compounds by Means of Sodium Bromate
Kanemoto, Shigekazu,Tomioka, Hiroki,Oshima, Koichiro,Nozaki, Hitosi
, p. 105 - 108 (2007/10/02)
Sodium bromate has been found to be effective oxidant for oxidation of alcohols in the presence of cerium or ruthenium compounds in biphase reaction.Selective oxidation of secondary alcohols was performed in the presence of primary ones using cerium(IV) ammonium nitrate (CAN) or cerium(IV) sulfate (CS) as catalyst.For instance, treatment of 1,10-undecanediol with CS/NaBrO3 provided 11-hydroxy-2-undecanone in 82percent yield.Ruthenium catalyzed biphase oxidation of alcohols with sodium bromate provided the corresponding aldehydes or ketones in good to excellent yields.
Cumulated Ylides, XII. A Stereoselective Synthetic Method for (Z)-α,β-Unsaturated Aldehydes
Bestmann, Hans Juergen,Roth, Kurt,Ettlinger, Manfred
, p. 161 - 171 (2007/10/02)
(2-Ethoxyvinyl)triphenylphosphonium bromide (5) is converted with sodium amide into the corresponding phosphaallenylide 6 which adds ethanol forming the ylide 7. 7 is also obtained by the reaction of 5 with sodium ethanolate.The Wittig reaction of 7 with aldehydes 2 proceeds with high (Z)-stereoselectivity to give (Z)-α,β-unsaturated acetals 8 which are cleaved under well defined conditions with p-toluenesulfonic acid or with wet silica gel to (Z)-α,β-unsaturated aldehydes 9.
