175689-47-1

Basic information

• Product Name: <1-(1,1-dimethylethoxycarbonyl)-2-pyrrolyl>ethyl 2-diazo-4-phenyl-3(E)-butenoate
• Synonyms: <1-(1,1-dimethylethoxycarbonyl)-2-pyrrolyl>ethyl 2-diazo-4-phenyl-3(E)-butenoate
• CAS NO: 175689-47-1
• Molecular Weight: 381.431
• Mol File: 175689-47-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: <1-(1,1-dimethylethoxycarbonyl)-2-pyrrolyl>ethyl 2-diazo-4-phenyl-3(E)-butenoate(CAS DataBase Reference)
• NIST Chemistry Reference: <1-(1,1-dimethylethoxycarbonyl)-2-pyrrolyl>ethyl 2-diazo-4-phenyl-3(E)-butenoate(175689-47-1)
• EPA Substance Registry System: <1-(1,1-dimethylethoxycarbonyl)-2-pyrrolyl>ethyl 2-diazo-4-phenyl-3(E)-butenoate(175689-47-1)

Safety Data

• Hazardous Substances Data: 175689-47-1(Hazardous Substances Data)

Upstream product

• 175689-46-0 2-(2-pyrrolyl)ethyl 4-phenyl-3(E)-butenoate 
• 60773-92-4 β-benzalpropionic acid chloride 
• 22186-60-3 2-(2-hydroxyethyl)-pyrrole 

Relevant articles and documents

Divergent pathways in the intramolecular reactions between rhodium-stabilized vinylcarbenoids and pyrroles: Construction of fused tropanes and 7-azabicyclo[4.2.0]octadienes

The rhodium(II)-catalyzed intramolecular reaction between vinyldiazomethanes and pyrroles leads to a novel synthesis of fused tropanes. The reaction occurs by a stepwse 3 + 4 annulation mechanism between a rhodium-stabilized vinylcarbenoid intermediate and the pyrrole rather than by the typical tandem cyclopropanation/Cope rearrangement sequence. The outcome of the reaction is very sensitive to the vinylcarbenoid structure. In particular, the presence of a 2-siloxy substituent on the vinylcarbenoid strongly favors the formation of fused tropanes. In the absence of such functionality, the formation of fused 7-azabicyclo[4.2.0]octadienes becomes the dominant reaction pathway.