280763-58-8Relevant academic research and scientific papers
Intramolecular [4 + 2] Cycloaddition Reactions of Diarylacetylenes: Synthesis of Benzo[b]fluorene Derivatives via Cyclic Allenes
Rodríguez, David,Navarro, Armando,Castedo, Luis,Domínguez, Domingo,Saá, Carlos
, p. 1497 - 1500 (2000)
(Equation Presented) 2-Propynyldiarylacetylenes undergo thermal intramolecular [4 + 2] cycloaddition to give benzo[b]fluorene derivatives in good yields. The hybridization of the tether connecting the reacting alkynes has a pronounced effect on the course
Synthesis and inclusion properties of 6,6′-Bi(benzo[b]fluoren-5-ol) derivative by cycloaromatization
Kawano, Tomikazu,Suehiro, Masako,Ueda, Ikuo
, p. 58 - 59 (2007/10/03)
Aromatic non-conjugated tetraynes underwent step-by-step cycloaromatization to yield 6,6′-bi(benzo[b]fluoren-5-ol) derivative 1 via benzo[b]fluoren-5-ol derivatives. Treatment of compound 1 with a kind of organic guest compounds afforded crystalline inclusion compounds (clathrates). Copyright
A new rearrangement of cyclic allenes via 1,2-dehydro[10]annulenes: Formation of benzo[c]fluorenones
Rodríguez, David,Navarro-Vázquez, Armando,Castedo, Luis,Domínguez, Domingo,Saá, Carlos
, p. 2717 - 2720 (2007/10/03)
A new rearrangement of cyclic allenes giving benzo[c]fluorenones was observed when studying intramolecular dehydro Diels-Alder reactions of silyl-substituted alkynes with arenynes (aryldiacetylenes).
Oxyanion-Accelerated C2-C6 Cyclization of Benzannulated Enyne-allenes
Brunette, Steven R.,Lipton, Mark A.
, p. 5114 - 5119 (2007/10/03)
The cyclization of oxyanion-substituted, benzannulated enyne-allenes was found to proceed rapidly and efficiently at room temperature, producing substituted indanones and fluorenones through a C2-C6 cyclization pathway. These reactions bear close resemblance to thermal C2-C6 cyclizations of enyne-allenes previously reported by Schmittel and others, though the oxyanion-substituted cases cyclize far more rapidly, and stand in noteworthy contrast to the C2-C7 (Myers) cyclization of (Z)-1,2,4-heptatrien-6-yne, the parent enyne-allene. The rate of reaction was found to be sensitive to the size of the alkyne and allene substituents, though the electronic effects of substitution are not known. The acceleration imparted by the oxyanion substituent is consistent with the electronic stabilization of a proposed diradicaloid transition state for the C2-C6 cyclization, but the available evidence does not permit the distinction between concerted and stepwise mechanisms. Studies are ongoing to further elucidate the mechanism and expand the scope of these transformations.
