437656-93-4

Usage

Type

Diazo compound

Appearance

Yellow to red solid

Storage

Sensitive to light, should be stored in a dark place

Reactivity

Can undergo cyclopropanation, aziridination, and carbene insertion reactions

Use

Commonly used as a diazo transfer reagent in organic synthesis

Products

Can lead to the formation of various functionalized organic compounds

Safety

Extremely sensitive to shock and friction, should be handled with extreme caution and under appropriate safety measures.

Upstream product

• 123-76-2 levulinic acid 
• 1117-96-0 Diazoethan 
• 352017-17-5 C₁₀H₁₆O₅ 

Downstream Products

• 817165-31-4 1,8-dimethyl-5,9-dioxatricyclo[5.2.1.0^4,8]decane-4,7-diol 
• 817165-33-6 1,5-dimethyl-2-(1,3-dioxan-2-yl)-7-methylene-8-oxabicyclo[3.2.1]octane 

Relevant academic research and scientific papers

Stereocontrolled syntheses of the nemorensic acids using 6-diazoheptane-2,5-dione in carbonyl ylide cycloadditions

Levulinic acid-derived 6-diazoheptane-2,5-dione (9) serves as a common precursor in a formal synthesis of frontalin 19, and in syntheses of cis-nemorensic acid 1, 4-hydroxy-cis-nemorensic acid 2, 3-hydroxy-cis-nemorensic acid 3, and nemorensic acid 4. The key step in these syntheses is the Rh 2(OAc)4-catalyzed tandem carbonyl ylide formation-intermolecular 1,3-dipolar cycloadditions of diazodione 9 with formaldehyde, alkynes or allene, which occur with high regioselectivity. Subsequent oxidative cleavage of the ring originally derived from the cyclic carbonyl ylide intermediate provides a straightforward access to polysubstituted tetrahydrofurans, and in particular an efficient entry to the nemorensic acids. Enantioselective cycloadditions with diazodione 9, using chiral rhodium catalysts, gave cycloadducts in up to 51% ee.