Functionalization of saturated hydrocarbons. High temperature bromination of octahydropentalene. Part 19

Gunbas, DD
Algi, F
Hokelek, T
Watson, WH
Balcı, Metin
The synthesis and thermal bromination of octahydropentalene was studied. The reaction afforded 1a,3a,4b,6b-tetrabromo-1,2,3, 4,5,6-hexahydropentalene (14) with remarkable regio- and stereospecificity. The structure of the product was determined by H-1 and C-13 NMR data and single X-ray structural analysis. The treatment of octahydropentalene with tenfold bromine gave the octabromopentalene derivative. The formation mechanism of the products is discussed.


Synthesis of ferrocenyl quinones
Zora, Metin; Acikalin, S (Elsevier BV, 2003-03-03)
A squarate-based synthesis of ferrocenyl quinones is described. Thermolysis of ferrocenyl-substituted cyclobutenones, prepared from ferrocenyl cyclobutenediones and alkenyllithiums, affords hydroquinones, which furnish, upon oxidation, ferrocenyl quinones. Ferrocenyl cyclobutenediones have been prepared from known cyclo butenediones by nucleophilic addition of ferrocenyllithium followed by hydrolysis, Pd/Cu-cocatalyzed cross-coupling with (tri-n-butylstannyl)ferrocene or Friedel-Crafts alkylation with ferro...
Synthesis of 2-ferrocenylidene-4-cyclopentene-1,3-diones
Zora, Metin; Eralp, Tugce (Elsevier BV, 2006-10-29)
A squarate-based synthesis of 2-ferrocenylidene-4-cyclopentene-1,3-diones is described. When refluxed in dioxane at 100 degrees C, heated with silica gel as a solvent free grinded solid mixture at 125 degrees C or stirred with silica gel in ethyl acetate at room temperature, 4-ferrocenylethynyl-4-hydroxy-2-cyclobutenones, prepared from ethynylferrocene and 3-cyclobutene-1,2-diones, afforded 2-ferrocenylidene-4-cyclopentene-1,3-diones as the major or single product of the reaction. In some cases, ferrocenyl ...
Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones
Demir, Ayhan Sıtkı; Aybey, Asuman (Elsevier BV, 2008-12-01)
The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords ph...
Chemistry of dioxine-annelated cycloheptatriene endoperoxides and their conversion into tropolone derivatives: an unusual non-benzenoid singlet oxygen source
Dastan, A; Balcı, Metin (Elsevier BV, 2006-04-24)
The chemistry of two bicyclic endoperoxides, obtained by photooxygenation of 2,3-dihydro-7H-cyclohepta[1,4]dioxine and 2,3-dihydro-7H-cyclohepta[b][1,4]dioxin-7-one was investigated with the aim of synthesizing the respective tropolone derivatives. The reaction of these endoperoxides with base, thiourea and their thermolysis provided the desired tropolone derivatives in high yield. On the other hand, the thermolysis of the endoperoxide derived from 2,3-dihydro-7H-cyclohepta[b] [ 1,4]dioxin-7-one underwent a...
Distyryl-boradiazaindacenes: facile synthesis of novel near IR emitting fluorophores
Dost, Zeynep; Atilgan, Serdar; Akkaya, Engin U. (Elsevier BV, 2006-09-04)
Boradiazaindacenes with methyl substituents at 3 and 5 positions were for the first time shown to undergo efficient double condensation reactions with an aromatic aldehyde yielding a series of extended conjugation dyes. These new fluorophores have absorption maxima in the range of 650-660 nm. The dyes reported here have large quantum yields with 20 nm Stokes' shifted emission peaks. The straightforward synthesis of such red shifted BODIPY derivatives is important in relation to the synthesis of novel and us...
Citation Formats
D. Gunbas, F. Algi, T. Hokelek, W. Watson, and M. Balcı, “Functionalization of saturated hydrocarbons. High temperature bromination of octahydropentalene. Part 19,” TETRAHEDRON, pp. 11177–11183, 2005, Accessed: 00, 2020. [Online]. Available: