35202-08-5

Upstream product

• 108-24-7 acetic anhydride 
• 555-16-8 4-nitrobenzaldehdye 
• 463-51-4 Ketene 
• 953-26-4 ethyl 4-nitrocinnamate 
• 75-36-5 acetyl chloride 
• 127146-25-2 acetic anhydride carbanion 
• 57999-52-7 3-Bromo-3-(p-nitrophenyl)propionic acid 

Downstream Products

• 61960-78-9 1-[3-hydroxy-3-(4-nitro-phenyl)-propionyl]-piperidine 
• 100-13-0 4-nitrostyrene 
• 15719-64-9 methylammonium carbonate 
• 619-89-6 p-nitrocinnamic acid 
• 57999-52-7 3-Bromo-3-(p-nitrophenyl)propionic acid 

Relevant academic research and scientific papers

β-LACTONE AS INTERMEDIATE IN THE PERKIN REACTION CATALYZED BY TERTIARY AMINES

The Perkin reaction catalyzed by tertiary amines is found to run not according to the aldol-type condensation mechanism but according to the mechanism in which the first stage is the formation and cycloaddition of ketene, yielding a β-lactone, which cleaves to the unsaturated acid.

Direct acylation of carrier proteins with functionalized β-lactones

As the key component of many biosynthetic assemblies, acyl-carrier proteins offer a robust entry point for introduction of small molecule probes and pathway intermediates. Current labeling strategies primarily rely on modifications to the phosphopantethei

A one-pot synthesis of 3-arylglutaric anhydrides by reaction of ketene with aromatic aldehydes and ketones

Aromatic aldehydes and ketones react with ketene under Lewis acid catalysis to produce β-lactones, which in situ react with another molecule of ketene to produce 3-arylglutaric anhydrides. The mechanism, scope, and limitation of this one-pot synthesis of 3-substituted glutaric anhydrides are discussed.

Studies of the asymmetric [2+2] cycloaddition of silylketenes and aldehydes employing Ti-TADDOL catalysts

Ti-TADDOL catalysts provide good reactivity and moderate enantioselectivity in the asymmetric [2+2] cycloaddition of silyl ketenes and aldehydes. The effects of potential bidentate chelation of benzyloxy substituted aldehydes and of the steric size of the ketene silyl group were studied.

GENERATION AND PROPERTIES OF ACETIC ANHYDRIDE CARBANION

In the reaction between ketene and acetate ions the labile acetic anhydride carbanion is formed.This carbanion generated in situ in the presence of 4-nitrobenzaldehyde undergoes cycloaddition yielding β-lactone and, further, 4-nitrocinnamic acid (Path A).It can also undergo numerous inter- and intramolecular reactions producing various by-products, i.e.CO2, acetoacetic acid (tetrabutylammonium salt), propen-2-ol acetate, acetone, acetylacetone (Path B).Analogical products were obtained with carbanion generated from acetic anhydride by sodium hydride.