83967-98-0

Upstream product

• 75233-61-3 2-(2-nitroethoxy)tetrahydro-2H-pyran 
• 110-87-2 3,4-dihydro-2H-pyran 
• 100-42-5 styrene 
• 77790-67-1 (tetrahydropyran-2-yl)oxyacetonitrile oxide 

Downstream Products

• 26613-71-8 4-phenyl-2-methylenebutyrolactone 
• 83670-90-0 1,4-Dihydroxy-4-phenyl-butan-2-one 
• 87044-52-8 1-Phenyl-3-(tetrahydro-pyran-2-yloxymethyl)-but-3-en-1-ol 
• 83670-85-3 4,5-dihydro-3-(hydroxymethyl)-5-phenylisoxazole 

Relevant academic research and scientific papers

The Isoxazoline Route to α-Methylene Lactones.

A new route to α-methylene lactones, important structural subunits of many natural products, has been developed using the nitrile oxide derived from 2-nitroethanol.

Methods for the Stereoselective Cis Cyanohydroxylation and Carboxyhydroxylation of Olefins

Two valuable reagents for the cis-specific vicinal cyanohydroxylation and carboxyhydroxylation of olefins are described.The cyanohydroxylation process is based on the decarboxylative ring opening of 3-carboxyisoxazolines prepared by the cycloaddition reaction of carbethoxyformonitrile oxide with various alkenes.Fragmentation of the isoxazolines prepared from cis- and trans-2-butene has been found to occur without any crossover in stereochemistry.The carboxyhydroxylation process begins with the dipolar cycloaddition reaction of the nitrile oxide derived from thetetrahydropyranyl ether derivative of 2-nitroethanol.Deprotection, hydrogenation, and oxitative cleavage of the derived dihydroxy ketone yield the stereochemcally pure β-hydroxy carboxylic acid.