71084-47-4

Upstream product

• 71084-46-3 2-(2,2-Diethoxy-ethoxy)-1,3-dimethoxy-benzene 
• 61413-50-1 1-(4-hydroxy-3-methoxyphenyl)-2-(2,6-dimethoxyphenoxy)-propane-1,3-diol 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 

Downstream Products

• 91657-65-7 N,N'-bis(ω-(2',6'-dimethoxyphenoxyethylamino)hexyl)cystamine 
• 91657-66-8 N,N'-bis(ω-(2',6'-dimethoxyphenoxyethylamino)heptyl)cystamine 
• 91657-64-6 N,N'-bis(ω-(2',6'-dimethoxyphenoxyethylamino)pentyl)cystamine 
• 449195-19-1 2-[benzyl[2-(2,6-dimethoxyphenoxy)ethyl]amino]-1-ethanol 
• 770703-33-8 N-benzyl-N-[2-(2,6-dimethoxyphenoxy)ethyl]amine 

Relevant academic research and scientific papers

Organocatalytic Chemoselective Primary Alcohol Oxidation and Subsequent Cleavage of Lignin Model Compounds and Lignin

A one-pot two-step degradation of lignin β-O-4 model compounds initiated by preferred oxidation of the primary over the secondary hydroxyl groups with a TEMPO/DAIB system has been developed [TEMPO=2,2,6,6-tetramethylpiperidine-N-oxyl, DAIB=(diacetoxy)iodobenzene]. The oxidised products are then cleaved by proline-catalysed retro-aldol reactions. This degradation methodology produces simple aromatics in good yields from lignin model compounds at room temperature with an extension to organosolv beech-wood lignin (L1) resulting in known cleavage products.

Singlet oxygen in the photodegradation of lignin models

The photochemical oxidation of lignin models in the presence of singlet oxygen was studied. The treatment of the non-phenolic β-O-4 aryl ether derivatives 6, 7, and 8 in the presence of both oxygen and Rose Bengal gave products deriving from a formal β-C-O cleavage formation. By this way. the derivatives 12, 13, and 15 were obtained. The photochemical oxidation of the phenolic β-O-4 aryl ether 9 gave the same type of product confirming that, in this case, the presence of the carbonyl group is not indispensable to have the cleavage reaction. The use of the model compound 10 showed that, when the phenoxy part of the molecule shows a lower reactivity towards singlet oxygen, the oxidation of the phenol moiety to hydroquinone call occur. The photochemical behaviour of these model compounds can be rationalised from a reaction of singlet oxygen with the phenoxy part of the molecule.