Browsing by Author "Lewis, Linda Kay"

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    Synthesis of functionalized naphthalenes
    (1983) Lewis, Linda Kay; Billings, W. E.; Engel, Paul S.; Lewis, Edward S.
    1,2 and 2,3-disubstituted naphthalenes were synthesized by carbene addition to substituted indenes. The indene precursors were formed by two methods: Grignard addition to indanones with elimination and by the reaction of indanones with phosphorus pentahalide. The carbene addition to indene was facilitated fcy the use of a micellar phase transfer catalyst, hexadecyltrimethyl ammonium branide. This catalyst allowed carbene addition to double bonds with both electron donating and withdrawing substituents. The naphthalenes formed by this method include: 2-chloro-3-methylnaphthalene, 2-chloro-3-phenylnaphthalene, 1,2-dichloronaphthalene, 2-chloro-l-phenylnaphthalene, 2-brano-3chloronaphthalene and 2,3-dichioronaphthalene.