113549-27-2

Upstream product

• 3376-23-6 N-methyl-α-phenylnitrone 
• 2525-42-0 phenylsulfonylpropa-1,2-diene 
• 3376-23-6 N-(benzylidene)methylamine N-oxide 
• 107402-95-9 2-methyl-3-phenyl-4-(phenylsulfonyl)-5-methyleneisoxazolidine 
• 75-03-6 ethyl iodide 
• 113854-20-9 (Pent-1-yne-1-sulfonyl)-benzene 

Downstream Products

• 82297-62-9 (E)-1-phenylhex-1-en-3-one 
• 29898-25-7 1-phenylhexan-3-one 
• 113549-28-3 1-phenyl-2-(phenylsulfonyl)-hex-1-en-3-one 
• 118987-60-3 2,4-dimethyl-3-phenyl-4-phenylsulphonyl-5-propylideneisoxazolidine 

Relevant academic research and scientific papers

ALKYATION STUDIES OF 5-EXO-METHYLENE SUBSTITUTED ISOXAZOLIDINES

1,3-Dipolar cycloaddition of nitrones to phenylsulphonylallene gives in high yield and with complete regiospecificity 5-methyleneisoxazolidines.These on treatment with base and subsequent reaction with electrophiles afford both α- and γ-substituted products.With methyl iodide as the electrophile, only the α-methylated product was isolated.In contrast, reaction of the 5-exo-methylene-4-phenylsulphonylisoxazolidine with allyl bromide afforded the γ-allyated product.Formation of this was shown to be via direct γ-attack, rather than by α-attack, followed by a 3,3-sigmatropic rearrangement.Further studies show that the product ratio is controlled by a sensitive interplay between thermodynamic and steric factors and is very dependent on the nature of the electrophile used.

ISOXAZOLINE OXIDATION. AN EFFICIENT METHOD FOR THE PREPARATION OF α,β-UNSATURATED CARBONYL COMPOUNDS

MCPBA peracid oxidation of Δ4-isoxazolines derived from the dipolar cycloaddition reaction of nitrones with acetylenes or allenes produces α,β-unsaturated ketones in excellent yield.

DIPOLAR CYCLOADDITION REACTION OF (PHENYLSULFONYL)PROPADIENE WITH NITRONES AND ALKYLATION STUDIES OF THE CYCLOADDUCTS

Dipolar cycloaddition of nitrones with (phenylsulfonyl)propadiene give 4-sulfonyl substituted isoxazolidenes whose reactions with base and several electrophiles have been studied.