97268-04-7

Upstream product

• 25857-78-7 1-phenylmethyl-4N-acetylimino-1H-1,2,4-triazolium betain 
• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 89373-98-8 C₂₁H₂₂N₄O₆ 

Relevant academic research and scientific papers

SITE-SELECTIVITY OF 1,3-DIPOLAR CYCLOADDITIONS TO 2,3-DIMETHOXYCARBONYL-7-OXABICYCLO-HEPTADIENE

Site-selectivity of dipolar cycloaddition to the title compound was studied.Azomethine X afforded a 1:1 cycloadduct XI at the deactivated double bond at room temperature;upon thermolysis at 110 degC it afforded the acetylated enamine XIII, wich was formed wia a direct cycloaddition at the mentioned temperature.The cycloaddition course was investigated in various solvents;the enamine XIV formed by solvolysis of XIII was the final products in methanol.Cycloaddition of title compound to azides, benzoylnitrile N-oxide and C-acetyl-N-phenylnitrilimine furnished the product of cycloreversion instead of the not isolable 1:1 cycloadducts.5-Azido-2-furancarbaldehyde and 4-nitrophenylazide yielded cycloaddition products to both multiple bonds in an approximately 1:1 ratio: HN3, tosylazide,benzoylnitrile N-oxide and C-acetyl-N-phenylnitrilimine gave the addition products to the deactivated double bond.The solvent-effect of site-selectivity of 1,3-dipolarcycloaddition was inwestigated and the title compound was found to be an exellent synthetic equivalent for acetylene and dimethyl butinedioate.