Browsing by Author "Billings, W. E."

Now showing 1 - 3 of 3
  • Thumbnail Image
    Item
    Palladium catalysed oligomerization of 1-alkynes
    (1975) Hunt, Ann Louise Beal; Billings, W. E.
    The oligomerization of 1-pentyne using palladium acetyl acetonate catalyst with various solvents and ligands was investigated. An equimolar mixture of HOAc and Et N proved to be a superior solvent. The major product observed in most cases was the dimer, 6-methylene-nona-yne, although both cis and trans-dect-ene-6-yne were observed in most cases. Trimers were formed when phosphines were replaced with bldentate amines or phosphite ligands. A one to one mixture of PPh and (CH ) P gave the highest yield of oligomers with 6-methylene-nona-4-yne as the major product. No aromatics were formed with any of the reaction systems studied. The general mechanism proposed, by Meriwether and elaborated by Maitlis is in agreement with these results.
  • Thumbnail Image
    Item
    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.
  • Thumbnail Image
    Item
    The effect of ring size on the thermal rearrangements of bicyclo[n.1.0] alka-1, n-dienes
    (1974) Baker, Brian Austin; Billings, W. E.
    The ring expansion synthesis of cycloundacene from cyclooctene Is described» Addition of dlbromocarbene, elimination/rearrangement by n-BuLl to an aliene, and Na/NH reduction results In the formation of the next larger cycloolefin. The synthesis and rearrangements of the title compounds n-7-1 are discussed. Compound 7 rearranges exclusively to 3-methylene-1,4-cyclononadiene. Compounds 9 & 1 rearrange to 4-methylenebicyolo. Compound 8 rearranges to a 1-2 mixture of 3-methylene-l-4-cyclodecadiene and 4-methylenebicyclo deca-2-ene respectively. This is the slowest material to rearrange requiring sixteen hours at xylene reflux whereas the others rearrange within several hours in toluene reflux.