72038-67-6

Usage

InChI:InChI=1/C6H8O2/c1-2-3-4-5-6(7)8/h3H,1,4-5H2,(H,7,8)

Upstream product

• 5558-05-4 5-bromo-1,2-pentadiene 
• 124-38-9 carbon dioxide 
• 82430-88-4 hexa-4,5-dien-1-nitrile 
• 24767-71-3 3,4-pentadien-1-ol tosylate 
• 40365-64-8 hexa-4,5-dien-1-ol 
• 925-90-6 ethylmagnesium bromide 
• 106-96-7 propargyl bromide 
• 20521-51-1 hexa-4,5-dienal 

Downstream Products

• 41143-12-8 hex-4-ynoic acid 
• 121224-96-2 5-(1-Phenyl-vinyl)-dihydro-furan-2-one 
• 29393-32-6 γ-acetyl-γ-butyrolactone 
• 1177428-43-1 Se-phenyl 4,5-hexadienecarboselenoate 
• 37244-00-1 (3E,8S,11E,16S)-8,16-bis(2-oxopropyl)-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetraone 

Relevant academic research and scientific papers

Regioselective Intramolecular Allene Amidation Enabled by an EDA Complex**

The addition of radicals to unsaturated precursors is a powerful tool for the synthesis of both carbo- and heterocyclic organic building blocks. The recent advent of mild ways to generate N-centered radicals has reignited interest in exploiting highly regio-, chemo-, and stereoselective transformations that employ these reactive intermediates. While the additions of aminyl, iminyl, and amidyl radicals to alkenes and alkynes have been well-studied, analogous additions to allenes are scarce. Allenes offer several attractive features, including potential for selective amidation at three distinct sites via judicious choice of precursor or radical source, the opportunity for axial-to-point chirality transfer, and productive trapping of vinyl or allyl radical intermediates to diversify functionality in the products. In this article, we report a regioselective addition of amidyl radicals to allenes to furnish an array of valuable N-heterocycle scaffolds.

Cp2ZrCl2-mediated three-component coupling reactions of CO2, ethylene (or alkynes), and electrophiles leading to carboxylic acid derivatives

Zirconacycles 1 and 2 can be simply generated from Cp2ZrCl 2, EtMgBr, and an atmospheric pressure of CO2. The treatment of Cp2ZrCl2 with EtMgBr followed by exposure to CO2 generates zirconacycle 1, which can react with various electrophiles to give a variety of carboxylic acid derivatives. Unsaturated zirconacycles 2 can also generated from Cp2ZrCl2, EtMgBr, alkynes, and CO2. Complexes 2 react with electrophiles to give α,β-unsaturated acids stereoselectively.

Acylation-cyclization of allenes

Allenes bearing a nucleophilic group cyclize on treatment with acyltetracarbonyl cobalt complexes in the presence of mild bases. Various nucleophilic groups and cobalt complexes can be used to give highly functionalized pyrrolidines, cyclopentanes and tet