Diels-Alder reaction of isobenzofurans

The IR, UV, H NMR, C NMR, and mass spectra of several benzo[c]furan derivatives, (272-273). <83CJC1987>, (274) <86JOC3973>, (275-279) <82JOC409> and (280-281) <84JCS(Pl)859> have been used to elucidate structural features concerning the Diels-Alder reaction of isobenzofurans with dienophiles the endo exo ratios were readily estimated by H NMR since the differences between the isomers are typical of all Diels-Alder adducts. 

Reactions where 1,3-diarylisobenzofuran derivatives act as the diene component in Diels-Alder reactions are well known and new routes have been developed, especially to isobenzofurans that are oxygenated in the benzenoid ring <8773681, 89BSF44i>. Diels-Alder reactions of isobenzofurans... 

Isobenzofurans are reactive Diels-Alder dienes, and they have been used for the construction of aromatic skeletons extensively [26]. A mixture of endo/exo cycloadducts obtained from the Diels-Alder reaction of isobenzofuran with a variety of dienophdes underwent dehydration under acidic conditions to give aromatic compounds. Isobenzofuran was generated in situ in the reaction by the loss of ethanol from the starting material cyclic acetal (Scheme 16.25) [27]. Using the approach in Scheme 16.25, a variety of naphthalimides have been synthesized that find application in DNA detection and white light-emitting OLEDs [28]. 

---