99529-42-7

Basic information

• Product Name: N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide
• Synonyms: N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide
• CAS NO: 99529-42-7
• Molecular Weight: 179.175
• Mol File: 99529-42-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide(99529-42-7)
• EPA Substance Registry System: N-methyl-10-oxabicyclo[2.2.1]hept-8-ene-3,endo-5-endo-dicarboximide(99529-42-7)

Safety Data

• Hazardous Substances Data: 99529-42-7(Hazardous Substances Data)

Upstream product

• 155793-97-8 endo,endo-2,3-dibromo-7-oxanorborneno<2,3-c>succinimide 
• 110-00-9 furan 
• 930-88-1 N-methylmaleimide 

Relevant articles and documents

Evidence for an Olefinic Intermediate in the Configurational Inversion Accompanying Hydrogenolysis of a 7-Oxanorbornyl Vicinal Dibromide

The endo,endo-2,3-dibromo-7-oxanorbornenosuccinimide (1) undergoes complete inversion upon hydrogenolysis of the bromine substituents to form (5) (Zn/Ag couple in THF) or (26) (H2, Pd/C).The highly reactive dienophile, N-methyl 7-oxanorbornadienomaleimide (3) is shown to be a transient intermediates in the Zn/Ag couple experiments by trapping with furan.Deuterium labelling experiments have been used to help elucidate the mechanism of these reactions.

Reductive heck reactions of N-methyl-substituted tricyclic imides

The palladium-catalyzed hydroarylation of N-methyl-substituted tricyclic imides was studied in order to find a new stereoselective access to a series of new exoaryl(hetaryl)-substituted tricyclic N-methylimides.

Unusual Stability of N-Methylmaleimide Cycloadducts: Characterization of Isobenzofuran Retro-Diels-Alder Reactions

Many years ago Diels and Thiele noted the unusual stability of maleic anhydride cycloadducts and employed this feature in scavenging anthracene generated in a retro- reaction.N-methylmaleimide, although nearly identical to maleic anhydride in rates of Diels-Alder reactions, forms even more stable cycloadducts.The rate constants for the four reactions that characterize the furan/N-methylmaleimide system were measured under the conditions used by Lee and Herndon to study the furan/maleic anhydride system.Comparison of the two dienophiles indicates thatN-methylmaleimide adducts are ca. 3 kcal*mol-1 more stable than the corresponding exo- and endo-maleic anhydride adducts.Somewhat larger (ca. 4 +/- 0.5 kcal*mol-1) differences in stability were found for the cycloadducts of the much more reactive diene isobenzofuran.N-Methylmaleimide is used as a diene scavenger to obtain rate constants for retro-Diels-Alder reactions of isobenzofuran adducts with maleic anhydride and some substituted analogs.The rates of retro-Diels-Alder reactions of substituted N-methylmaleimide adducts were also determined by an alternative method.The substituents examined enhance the rates of exo retro-Diels-Alder reactions by factors of 15-40, while endo adduct retro-Diels-Alder rates are only slightly affected.Calculations were done at the MP2/6-31G*//HF/6-31G* level to compare the heats of hydrogenation of maleic anhydride and maleimide.The reduction of maleimide is calculated to be 2.5 kcal*mol-1 more exergonic, supporting the experimental observations.