5-Norbornene-endo-2,3-dicarboxylic anhydride

A soln. of hydroxylamine prepared by addition of Na-carbonate to an aq. soln. of hydroxylamine hydrochloride, 5-norbornene-endo-2,3-dicarboxylic anhydride... 

The Diels-Alder reaction is stereo specific. The stereochemistry of the dienophile is retained in the product i.e., cis and trans dienophiles produce different diastereoisomers in the product. For example, freshly distilled cyclopentadiene, having s-cis configuration, reacts with maleic anhydride to give c/ -norbornene-Sjh-endo-dicarboxylic anhydride. 

Cyclopentadiene and maleic anhydride react readily in a Diels—Alder reaction to form the adduct, ds-norbornene-5,6-endo-dicarboxylic anhydride ... 

Ring strain (cyclic anhydrides) moves the absorptions to the left. Stretch is at 1300-900 cm h The spectrum of cis-norbornene-5,6-endo-dicarboxylic anhydride is shown in Figure 25.37. 

CsHflOa, 5-Norbornene-2,3-endo-dicarboxylic anhydride, 34B, 304 C9H9KO8 1-5 H2O, Potassium hydrogen norborn-5-ene-2-endo,3-endo-dicarboxylate sesquihydrate, 42B, 151 C9HioBr20, 2,7-Dibromotricyclo[4.2.1.0 " ]nonan-4-one, 46B, 168 C9H10O8, Norborn-5-ene-2,3-endo-dicarboxylic acid, 39B, 135 C9H10O8, 5-Hydroxy-2,3-norbornane dicarboxylic acid 7-lactone, 39B, 135... 

The recrystallized CPD-MAH Diels-Alder adduct, endo-cis-nor-bornene-2,3-dicarboxylic anhydride, mp 165 C, was maintained at 220qC for 4 hr to yield a mixture of endo and exo anhydrides, mp 101 C. The crude product was recrystallized 3 times from benzene to isolate the exo isomer, mp 141UC. The endo- and exo-cis-N-phenyl-5-norbornene-2,3-dicarboximides, mp 144° and 197 C, respectively, were prepared by reaction of the endo- and exo-CPD-MAH adducts with aniline. 

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