[PDF] anthracene undergoes diels alder reaction

Anthracenes are well-known to undergo [4 + 2]-cycloadditions with dienophiles at their 9,10-positions (central ring) over 1,4-positions (terminal ring) guided by the relative aromatic stabilization energy of the two possible products, and also by harboring the largest orbital coefficients of the highest occupied
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  • What is the Diels-Alder reaction of anthracene mechanism?

    The reaction involves three ? bonds, two from the diene and one from the dienophile in a concerted reaction to form a six-membered ring. Since the reaction involves four ? electrons in the diene and two ? electrons from the dienophile, it is sometimes referred to as a 4 + 2 cycloaddition.

  • Why anthracene undergo Diels-Alder reaction but naphthalene does not?

    In Diels-alder reaction also, dienes which are aromatic are more stable and has less reactivity. For this reaction, high temperatures are required. Anthracene is less aromatic and this makes it more reactive as diene in Diels-alder reaction.

  • Does anthracene act as a diene?

    Anthracene, however, is an unusually unreactive diene. This is due to both steric effects, but more importantly because the “diene” is really part of an aromatic ring system and is thus stabilized. This stabilization in the reactant reduces the reactivity (stability/reactivity principle).
  • …maleic anhydride, butadiene undergoes the Diels-Alder reaction, forming cyclohexene derivatives. Butadiene is attacked by the numerous substances that react with ordinary olefins, but the reactions often involve both double bonds (e.g., addition of chlorine yields both 3,4-dichloro-1-butene and 1,4-dichloro-2-butene).
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