126580-09-4Relevant academic research and scientific papers
Reaction of β-trimethylsiloxy α-diazocarbonyl compounds with trimethylsilyl halides: A novel diazo decomposition process
Xiao, Fengping,Zhang, Zhenhua,Zhang, Jian,Wang, Jianbo
, p. 8873 - 8875 (2005)
When β-trimethylsiloxy α-diazocarbonyl compounds were treated with trimethylsilyl halide, a mixture of α- and γ-halide substituted unsaturated carbonyl compounds was obtained. The mechanism of this novel diazo decomposition process is discussed.
Deep eutectic solvent (DES) as dual solvent/catalyst for synthesis of α-diazocarbonyl compounds using aldol-type coupling
Miraki, Maryam Kazemi,Mehraban, Jamshid Azarnia,Yazdani, Elahe,Heydari, Akbar
, p. 129 - 132 (2017/04/01)
Deep eutectic solvent (DES) was employed as dual solvent/catalyst in the green synthesis of α-diazocarbonyl compounds using aldol-type coupling. α-Diazocarbonyl compounds are important synthetic intermediates with useful application for synthesis of amino alcohols and acids and many natural products. Moreover, the method is environmentally friendly because of avoidance of toxic solvents or hazardous catalysts.
A simple one-pot preparation of diazoacetoacetate derivatives from aldehydes
Erhunmwunse, Marvis O.,Steel, Patrick G.
experimental part, p. 8675 - 8677 (2009/04/11)
(Chemical Equation Presented) Diazoacetoacetate derivatives can be simply and efficiently prepared from aldehydes in a one-pot process involving initial DBU-promoted "aldol" condensation with ethyl diazoacetate followed by in situ oxidation with IBX. Aryl, alkyl, and unsaturated aldehydes are all viable substrates.
Catalytic aldol-type reaction of aldehydes with ethyl diazoacetate using quarternary ammonium hydroxide as the base
Varala, Ravi,Enugala, Ramu,Nuvula, Sreelatha,Adapa, Srinivas R.
, p. 877 - 880 (2007/10/03)
The direct aldol-type condensation of aldehydes with ethyl diazoacetate (EDA) promoted by an organic base and non-metallic catalyst such as tetrabutylammonium hydroxide (TBAOH) gave β-hydroxy-α-diazocarbonyl compounds with moderate to excellent yields. Furthermore, the reactivity and scope of various phase-transfer catalysts as well as electronically divergent aldehydes are discussed.
Reaction of Carbonyl Compounds with Ethyl Lithiodiazoacetate. Studies Dealing with the Rhodium(II)-Catalyzed Behavior of the Resulting Adducts
Padwa, Albert,Kulkarni, Yashwant S.,Zhang, Zhijia
, p. 4144 - 4153 (2007/10/02)
The carbenoid intermediate derived by treating ethyl 2-diazo-4-phthalimidobutyrate with rhodium(II) octanoate undergoes transannular cyclization onto the adjacent imido carbonyl group.The resulting cyclic carbonyl ylide diploe was trapped with several dipolarophiles.In an attempt to prepare related substrates for cyclization studies, the reaction of ethyl lithiodiazoacetate with various aldehydes and ketones was studied.Treatment of the α-diazo-β-hydroxy ester derived from acetone or cyclopentanone with rhodium(II) octanoate gave rise to a β-keto ester.The exclusive phenyl shift encountered with acetophenone is in keeping with migration to an electron-deficient center.The reaction works well with acrolein, leading to high yields of 3-oxo-4-pentenoate.The 1,2-hydrogen shift pathway was found to proceed much faster than intramolecular cyclopropanation.Dehydration of the α-diazo-β-hydroxy esters generates vinyl diazo esters, which readily cyclize to 1H-pyrazoles on thermolysis.
