694-72-4

Usage

Uses

Used in Organic Chemistry:
BICYCLO(3.3.0)OCTANE is used as a building block for the synthesis of various organic compounds. Its unique bicyclic structure allows for the creation of complex molecules with specific properties, making it valuable in the development of new chemical entities.
Used in Pharmaceutical Industry:
BICYCLO(3.3.0)OCTANE is utilized as a key intermediate in the synthesis of pharmaceutical compounds. Its distinctive structure contributes to the design of novel drugs with potential therapeutic applications, enhancing the diversity of chemical space for drug discovery.
Used in Stereochemistry Research:
BICYCLO(3.3.0)OCTANE serves as a model for studying stereochemical phenomena. Its bicyclic nature provides opportunities to explore the effects of ring strain and conformational preferences on the properties and reactivity of molecules, furthering understanding in the field of stereochemistry.
Used in Organic Synthesis Education:
BICYCLO(3.3.0)OCTANE is employed as a teaching tool in organic synthesis courses. Its structure illustrates fundamental concepts of ring formation, strain, and stereochemistry, aiding in the education of students and researchers in organic chemistry.

InChI:InChI=1/C8H14/c1-3-7-5-2-6-8(7)4-1/h7-8H,1-6H2/t7-,8-

Upstream product

• 292-64-8 Cyclooctan 
• 3806-59-5 1,3-cyclooctadiene 
• 30294-54-3 dihydropentalene 
• 103620-47-9 Z-1-iodocyclooct-4-ene 
• 2388-10-5 lithium isopropoxide 
• 65494-11-3 C₁₅H₁₅N₂O₂S^(1-)*Na⁽¹⁺⁾ 
• 74744-62-0 1,1:3,3-bis(1,5-cyclooctandiyl)diboroxane 
• 7446-70-0 aluminium trichloride 
• 872-78-6 exo-(2-methyl)norbornane 
• 765-90-2 (+/-)-2endo-methyl-norbornane 
• 87968-76-1 trans-1,2-bis(2,2-dibromocyclopropyl)ethylene 
• 5259-72-3 cyclo-octa-1,5-diene 

Downstream Products

• 42044-07-5 2-cyclohexylnaphthalene 
• 91-20-3 naphthalene 

Relevant academic research and scientific papers

Highly Active Superbulky Alkaline Earth Metal Amide Catalysts for Hydrogenation of Challenging Alkenes and Aromatic Rings

Two series of bulky alkaline earth (Ae) metal amide complexes have been prepared: Ae[N(TRIP)2]2 (1-Ae) and Ae[N(TRIP)(DIPP)]2 (2-Ae) (Ae=Mg, Ca, Sr, Ba; TRIP=SiiPr3, DIPP=2,6-diisopropylphenyl). While monomeric 1-Ca was already known, the new complexes have been structurally characterized. Monomers 1-Ae are highly linear while the monomers 2-Ae are slightly bent. The bulkier amide complexes 1-Ae are by far the most active catalysts in alkene hydrogenation with activities increasing from Mg to Ba. Catalyst 1-Ba can reduce internal alkenes like cyclohexene or 3-hexene and highly challenging substrates like 1-Me-cyclohexene or tetraphenylethylene. It is also active in arene hydrogenation reducing anthracene and naphthalene (even when substituted with an alkyl) as well as biphenyl. Benzene could be reduced to cyclohexane but full conversion was not reached. The first step in catalytic hydrogenation is formation of an (amide)AeH species, which can form larger aggregates. Increasing the bulk of the amide ligand decreases aggregate size but it is unclear what the true catalyst(s) is (are). DFT calculations suggest that amide bulk also has a noticeable influence on the thermodynamics for formation of the (amide)AeH species. Complex 1-Ba is currently the most powerful Ae metal hydrogenation catalyst. Due to tremendously increased activities in comparison to those of previously reported catalysts, the substrate scope in hydrogenation catalysis could be extended to challenging multi-substituted unactivated alkenes and even to arenes among which benzene.

Catalytic dehydrogenation of cyclooctane with titanium, zirconium and hafnium metallocene complexes

Metallocene complexes in combination with cocatalysts like methylalumoxane (MAO) are not only excellent catalysts for olefin polymerization but also appropriate catalysts for the activation of alkanes in homogeneous (autoclave) and heterogeneous (fixed be

Catalytic thermal and photo-induced CH and CC activation reactions of alkanes with ansa amido functionalized half-sandwich complexes and methylalumoxane

In the literature most of the dehydrogenation reactions of alkanes are described as CH activation reactions of cyclooctane. The best results of CH activation reactions have been found for the reaction of MAO activated metallocene complexes and cyclooctane

Carbenes in Constrained Systems, 3. Solid-State Photolysis of Cycloheptane- and Cyclooctanespirodiazirine within Cyclodextrins and Zeolites

Inclusion complexes of cycloheptanespirodiazirine (1) and cyclooctanespirodiazirine (8) in α-, β-, and γ-cyclodextrin, and faujasite type zeolites (NaX and NaY), have been prepared.The guest-host complexes (1- and 8CD and 1- and 8zeolite) were irradiated with UV light in the solid state and the reaction products were separated from the host and analyzed.Product ratios from photolysis of complexes were compared with those obtained from pure compounds and in solution.Cycloheptanespirodiazirine (1) gives cycloheptene (2), bicycloheptane (3), and methylenecyclohexane (4).Photolysis products from cyclooctanespirodiazirine (8) are cyclooctene (9), bicyclooctane (10), and bicyclooctane (11). 10 results from a 1,5-C-H insertion reaction of the carbene derived from 8.As the cavity size of the cyclodextrins becomes larger, the formation of 10 seems to increase.In β-cyclodextrin and in non-polar solvents substantial amounts of azine were found.In addition to hydrocarbons, photolyses in zeolites afforded alcohols and small amounts of the corresponding ketones. - Keywords: Diazirines / Zeolites / Cyclodextrins / Photochemistry / Carbenes

Radiolysis of Cyclooctane with γ-Rays and Helium Ions

Iodine scavenging techniques have been used to examine the role of the cyclooctyl radical in the radiolysis of cyclooctane with γ-rays and with 5-20-MeV helium ions.In γ-radiolysis about 70percent of the total yield of 6.6 cyclooctyl radicals/100 eV are scavenged with E-4 M iodine, which agrees well with other studies on cycloalkanes that show most of the radicals produced in these systems react in the bulk medium at times longer than 1 μs.However, it is found that 2.5 radicals/100 eV (38percent) are produced by H atom precursors as copmpared to a value of 1.5 cyclohexyl radicals/100 eV (25percent) in cyclohexane.With 10-MeV helium ions (average LET of 106 eV/nm), only 8percent of the cyclooctyl radicals survive longer than a few microseconds due to the increased initial radical concentration in the helium ion track.The yield of the cross-bridged product bicyclooctane (pentalane) was found to be independent of iodine concentration up to 0.03 M with both types of radiation.However, the pentalane yield found with 10-MeV helium ions was only one-third of that found in γ-radiolysis.The most likely reason for this result is the decreased yield of singlet-state formation due to the enhanced probability of cross combination reactions of electron-cation pairs in the high-density region of the helium ion track.

Dehydrogenation of Cycloalkanes by Suspended Platinum Catalysts

Heterogenized cluster complex 52- and reduced platinum metal have catalyzed cyclooctane dehydrogenation at comparable rates, whereas dehydrogenoaromatization of ethylcyclohexane proceeded predominantly with the latter.Active-site ensembles for the formation of cyclooctene, bicyclooctane and aromatics were discussed on reference to the appropriate stretch of platinum metal atoms.

PHOTOCHEMISTRY OF BENZOCYCLOBUTENE

Photolysis of benzocyclobutene (1) in pentane solution at 254 nm yields 1,2-dihydropentalene (2) and 1,5-dihydropentalene (3) as the major isomeric products; formation of 2 and 3 is consistent with a "prebenzvalene"-carbene rearrangement mechanism.

Evidence for Single Electron Transfer in the Reduction of Organic Halides by Lithium Triethylborohydride

Product studies involving the reduction of cyclizable alkyl iodides and bromides, trapping of intermediate radicals by dicyclohexylphosphine, and direct EPR observation of radicals have been used to detect the occurence of a single electron transfer pathway in the reduction of these halides by lithium triethylborohydride.

BICYCLOOCTA-2,6-DIEN-8-YLIDENE (HOMO-7-NORBORNADIENYLIDENE), A "FOILED" CARBENE

Bicycloocta-2,6-dien-8-ylidene nearly exclusively rearranges by 1,2-vinyl migrations.The interaction with the double bond of the six-membered ring dominates.

EVIDENCE FOR SINGLE ELECTRON TRANSFER IN THE REACTION OF ALKOXIDES WITH ALKYL HALIDES

Evidence for a radical process in the reaction of lithium alkoxides with alkyl iodides was obtained by observation of cyclization of appropriate radical probes, by the trapping of radicals, and by EPR spectroscopic observations relating to the one electron donor properties of alkoxides.