79913-35-2

Upstream product

• 100-42-5 styrene 
• 21572-32-7 2-chloro-1-phenyl-ethanone oxime 
• 613-91-2 acetophenone oxime 
• 53441-57-9 1-chloro-1-nitroso-1-phenylethane 
• 61145-11-7 (1-nitroso-vinyl)-benzene 

Downstream Products

• 26977-07-1 (+/-)-1-phenyl-4-(phenylamino)butanol 
• 128710-18-9 C₁₆H₁₄⁽²⁾HNO 
• 80463-28-1 N(1-phenylcyclopropyl)-benzamide 
• 495-71-6 phenacylacetophenone 
• 107487-41-2 4-hydroxy-1,4-diphenylbutan-1-one 

Relevant academic research and scientific papers

Cleavage of 3-aryl-5,6-dihydro-4H-1,2-oxazines using zinc and aqueous chelating ethers: Efficient methodology for N-O bond cleavage

A mild and efficient methodology for single pot ring opening of 3-aryl-4H-1,2-oxazines to γ-hydroxy ketones was developed using zinc and aqueous chelating ethers. The ether acts as ligand and co-solvent for the reaction. The ability of zinc ions to form stable complexes with chelating ethers activates the zinc towards reduction. Water is the proton source.

A new method for the generation of α-nitrosoolefins from ketooximes and its application to the synthesis of 5,6-dihydro-4H-1,2-oxazine derivatives [1]

Reaction of ketooximes containing α-methylene group with chloramine-T followed by treatment with triethylamine leads to the formation of α-nitrosoolefins via α-nitrosochloride, which can react in situ intermolecularly with olefinic compounds to produce 5,

The Cycloaddition of α-Nitrosostyrenes to Olefins. Investigations of the Scope and Mechanism of the Reaction

Cycloaddition of α-nitrosostyrene (1a) to several substituted styrenes is shown to give 3-phenyl-5,6-dihydro-4H-1,2-oxazines (2) in moderate yield.Reactions with 4-nitro-α-nitrosostyrene (1b) give better yields of the corresponding adducts (3).The preferred conformations of the adducts are deduced from their n.m.r. spectra.The observed regio- and stereo-selectivities of the addition are interpreted in terms of one-step addition in which the olefins act as the donor components.The first example of a formal 1,3-dipolar addition of a vinyl nitroso compound is provided by the formation of the nitrone (5) as a minor product of the reaction of α-nitrosostyrene with 2-methoxypropene.The relative yield of this nitrone is not increased by the change to a more polar solvent, nor by the use of α-bromoacetophenone anti-oxime in place of the usual syn-isomer as the precursor of α-nitrosostyrene.It is suggested that this, and other minor products (4) isolated from the cycloadditions, may be formed because of steric inhibition of the usual Diels-Alder-type process.