Polynuclear aromatic hydrocarbons

Naphthalene

Reactions

Oxidation

Reduction

Aromatization (catalytic dehydrogenation)

Proton scavengers also work.

Electrophilic Substitution

Activating group directs substitution into the same ring. Deactivating directs substitution into other ring.

Synthesis of Naphthols

Synthesis of naphthalene derivatives by ring closure. Haworth synthesis

Notes:

• 1) A substituted benzene may be used and a b  substituted naphthalene obtained
• 2) The intermediate cyclic ketone can be treated with a Grignard reagent introducing a alkyl or aryl group into the a position.
• 3) The keto acid in the form of its ester can be treated with a Grignard reagent introducing a alkyl or aryl group into the a position.

Phenanthrene and anthracene

Reactions

Oxidation and reduction

Electrophilic attack