90625-67-5

Upstream product

• 1631-28-3 N-p-tolylphenylmaleimide 
• 56241-32-8 3-methylpyridinium benzoylmethylide 
• 16844-10-3 N-phenacyl-3-methylpyridinium bromide 

Downstream Products

• 90625-68-6 (3aS,4S,9aS,9bR)-4-Benzoyl-9-methyl-2-p-tolyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione 

Relevant academic research and scientific papers

Stereochemical Study on 1,3-Dipolar Cycloaddition Reactions of Heteroaromatic N-Ylides with Symmetrically Substituted cis and trans Olefins

Stereochemistry of the cycloadditions of twenty-four heteroaromatic N-ylides with several symmetrically substituted cis and trans olefins has been investigated.Cyclic and acyclic cis olefins cycloadd to the anti form of the ylides in a highly endo-selective manner giving almost quantitative yields of stereospecific endo 3+2 cycloadducts.N-Ylides stabilized with a substituent of carbonyl type react with trans olefins to form mostly two stereoisomeric 3+2 cycloadducts to the anti form of the ylides.In most cases, they undergo the stereospecific interconversion through a retro cycloaddition process, the isomer ratios and the easiness of transfromation depending upon the nature and size of substituents on the five-membered ring which has been built up in the cycloaddition step.On the other hand, N-ylides stabilized with a substituent of noncarbonyl type react with trans olefins to give stereospecific and stereoselective 3+2 cycloadducts as single isomers which are assigned as the cycloadducts to the syn form of the ylides.

STEREOSELECTIVE HYDROALKYLIDENATION OF OLEFIN WITH PYRIDINIUM METHYLIDES

Acid-catalyzed elimination of pyridine from the stereoselective cycloadducts between electron-deficient olefins and pyridinium methylides with ylide-stabilizing substituents offers a new type of C-C bond formation.