97204-10-9Relevant academic research and scientific papers
Electrophilicities of 1,2-disubstituted ethylenes
Allgaeuer, Dominik S.,Mayr, Herbert
supporting information, p. 2956 - 2963 (2014/05/20)
The kinetics of the reactions of maleic anhydride, N-methylmaleimide, fumaronitrile, diethyl fumarate, and diethyl maleate with pyridinium and sulfonium ylides were studied in DMSO at 20 C. All of the reactions were found to follow a second-order rate law
STEREOCHEMICAL FEATURES OF CYCLOADDITION OF HETEROAROMATIC N-YLIDES. SELECTIVE PARTICIPATION OF THE ANTI AND SYN YLIDES
Tsuge, Otohiko,Kanemasa, Shuji,Takenaka, Shigeori
, p. 355 - 358 (2007/10/02)
In the cycloaddition of heteroaromatic N-ylides to symmetrically substituted trans olefins, the anti ylide exclusively participates if the ylide is carbonyl-stabilized, while the syn ylide does if it has a substituent of non-carbonyl type.The cycloadducts
Stereochemical Study on 1,3-Dipolar Cycloaddition Reactions of Heteroaromatic N-Ylides with Symmetrically Substituted cis and trans Olefins
Tsuge, Otohiko,Kanemasa, Shuji,Takenaka, Shigeori
, p. 3137 - 3157 (2007/10/02)
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.
Stereochemical Study on 1,3-Dipolar Cycloaddition Reactions of Heteroaromatic N-Ylides with Unsymmetrically Substituted Olefinic Dipolarophiles
Tsuge, Otohiko,Kanemasa, Shuji,Takenaka, Shigeori
, p. 3320 - 3336 (2007/10/02)
Regioselectivity and stereoselectivity of the cycloadditions of heteroaromatic N-ylides with unsymmetrically-substituted olefins such as methyl-substituted cis olefins, and acrylate, the related olefins, trans nitro olefins, and other trans olefins have b
