Date of Graduation
Eberly College of Arts and Sciences
Kung K. Wang.
Under mild conditions, a derivative of 11H-benzo[ b]fluorine 76, was successfully synthesized through tandem cyclization of the corresponding enediynyl propargylic alcohol, 69. Condensation of the substituted indanone 67 with the lithium acetylide 23 furnished benzannulated enediynyl propargylic alcohol 69 in 1:1 diastereomeric ratio. Reduction of propargylic alcohol 69 with triethylsilane in the presence of trifluoroacetic acid gave benzannulated enediynes 70. Treatment of 70 with potassium tert-butoxide in refluxing toluene furnished alkene 74. Hydroboration of alkene 74 followed by iodination in the presence of base produced alkyl iodide 75. The alkyl iodide 75 with treatment of potassium tert-butoxide in THF underwent intramolecular cyclization, producing the polycyclic aromatic hydrocarbon 76 in 18% overall yield from substituted indanone 67.
Parbin, Elbin Sehnaz, "Synthesis of polycyclic aromatic hydrocarbons via benzannulated enediynyl alcohols" (2007). Graduate Theses, Dissertations, and Problem Reports. 2539.