4011-20-5

Usage

Uses

Used in Organic Synthesis:
(2E,4Z,6E)-9-oxabicyclo[6.1.0]nona-2,4,6-triene is used as a building block for the synthesis of complex organic molecules. Its highly reactive nature allows for the formation of various chemical bonds and the creation of diverse molecular structures.
Used in Pharmaceutical Compounds:
(2E,4Z,6E)-9-oxabicyclo[6.1.0]nona-2,4,6-triene is used as a key intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity enable the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
(2E,4Z,6E)-9-oxabicyclo[6.1.0]nona-2,4,6-triene is used as a subject of study in chemical research. Its bicyclic structure and multiple double bonds make it an interesting target for exploring new reaction mechanisms and developing innovative synthetic methods.
Used in the Chemical Industry:
(2E,4Z,6E)-9-oxabicyclo[6.1.0]nona-2,4,6-triene is used in the chemical industry for the production of various chemical products. Its versatility and reactivity make it a valuable component in the synthesis of a wide range of compounds used in different applications.

InChI:InChI=1/C8H8O/c1-2-4-6-8-7(9-8)5-3-1/h1-8H/b2-1-,5-3-,6-4-

Upstream product

• 93-59-4 Perbenzoic acid 
• 477773-51-6 cyclooctatetraene 
• 629-20-9 1,3,5,7-cyclooctatetraene 
• 73982-04-4 cis-1,4-dihydroxycyclooctane 
• 83931-97-9 7,8-dioxabicyclo<4.2.2>deca-2,4,9-triene 
• 37996-40-0 (1R(S),4S(R),Z)-cyclooct-2-ene-1,4-diol 
• 83931-97-9 7,8-dioxabicyclo<4.2.2>deca-2,4,9-triene 
• 6572-77-6 1α,4α,6α,9α,5,10-dioxatricyclo<7.1.0.0^4.6>deca-2,7-diene 
• 79-21-0 peracetic acid 

Downstream Products

• 57015-09-5 (5Z,8Z,10Z)-1,4-diphenyl-3,11a-dihydro-oxonino[4,5-d]pyridazine 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 122-78-1 phenylacetaldehyde 
• 72012-64-7 C₁₆H₁₃N₃O₃ 
• 81599-81-7 N-phenyl-4-oxa-8,9-diazatetracyclo<5.2.2.0^2,6.0^3,5>undec-10-ene-8,9-dicarboximide 
• 4277-29-6 cycloheptanecarboxaldehyde 
• 92-52-4 biphenyl 
• 13705-29-8 2,4,6-cycloheptatrienyl phenyl carbinol 
• 557768-20-4 (1R,4R)-4-ethyl-2,5,7-cyclooctatrien-1-ol 
• 557768-20-4 (1S,4S)-4-ethyl-2,5,7-cyclooctatrien-1-ol 
• 557768-22-6 trans-4-vinyl-2,5,7-cyclooctatrien-1-ol 
• 13705-28-7 Ethyl-(cyclohepta-2,4,6-trienyl)-methanol 
• 557768-20-4 trans-4-ethyl-2,5,7-cyclooctatrien-1-ol 

Relevant academic research and scientific papers

The reaction of cyclooctatetraene with dimethyldioxirane

The reaction of cyclooctatetraene with dimethyldioxirane leads to the formation of four diepoxides, three triepoxides, and two tetraepoxides. The structures of the triepoxides and tetraepoxides were confirmed by x-ray crystallographic analysis.

THE SYNTHESIS OF ENDOPEROXIDE OF CYCLOOCTATETRAENE VIA PHOTOSENSITIZED SINGLET OXYGENATION

7,8-Dioxabicyclodeca-2,4,9-triene (3), the hitherto unknown endoperoxide of cyclooctatetraene, was prepared via cycloaddition of singlet oxygen and characterized by spectroscopic and chemical means.

Catalytic enantioselective desymmetrization of COT-monoepoxide. Maximum deviation from coplanarity for an SN2′-cuprate alkylation

(Matrix presented) The first alkylative and enantioselective ring-opening of COT-monoepoxide (1) without the occurrence of any ring-contraction-isomerization by the use of in situ-formed organocuprates is reported. Because of the particular geometric constraint of compound 1, this work reports the largest deviation from coplanarity between the π-orbital of the double bond and the σ-bond connecting the leaving group ever observed for an SN2′-cuprate alkylation.

Novel (α,β-Epoxyalkyl)lithium Reagents via the Lithiation of Organyl-Substituted Epoxides

A series of epoxides bearing unsaturated organyl groups attached directly to the epoxy group was found to have sufficient kinetic acidity to undergo clean lithiation at low temperatures.Epoxides of the type is aryl, vinylic, acetylenic, alkoxycarbonyl, or cyano, were smoothly converted into by either t-BuLi or LDA in the temperature range of -80 to -115 deg C.The resulting (α,β-epoxyalkyl)lithium reagents could be transformed into a variety of substituted epoxides, such as R2C-CE(Un)-O, where E = D, R3Si, R3Sn, R, RCO, CO2H, or COH(R)2.In cases where Un is acyl, addition to the carbonyl, rather than lithiation, occurred preferentially.Attempted lithiations of aziridines and thiiranes led to extrusion of nitrogen and sulfur, respectively.Even the relatively stable intermediates generated at -90 deg C underwent carbenoid-like decomposition at higher temperatures to yield isomerization and intermolecular-insertion products.Observation of these processes gives direct corroboration of reaction mechanisms proposed for the base-promoted isomerizations of epoxides.

SYNTHESIS OF ENDOPEROXIDES DERIVED FROM CYCLOOCTATETRAENES VIA SINGLET OXYGENATION

Cyclooctatetraene (1) reacted with photo-generated singlet oxygen to give the endoperoxide 7,8-dioxabicyclodeca-2,4,9-triene(1a), which was further transformed to the cis-diepoxide 1b by catalytic rearrangement with Co-TTP to the unsaturated cis-di

-Cycloaddition of Singlet Oxygen and Phenyltriazolinedione with Bicyclonona-2,4,6-triene and Derivatives

The dienic reactivity of the bicyclononatrienes 1a (-isomer) and 1b (-isomer) and its oxa-derivative 6 (cyclooctatetraene epoxide) as well as 1,3,5-cyclooctatrienone (7), towards singlet oxygen (1O2) and phenyl-1,2,4-triazoline-3,5-dione (PTAD) as dienophiles has been investigated.Except for 1a, which affords the endoperoxide 9a in 60percent yield, the remaining substrates 1b, 6, and 7 do not react with 1O2.With PTAD 1a, 1b, 6, and 7 afford the urazoles 10a, 8b, 12c, and 11, respectively.Unusual is the fact that the bicyclotriene 1b leads only to the tri cyclic urazole 8b, the first example of this type of -cycloadduct of 1b, while the oxa-analog 6 affords only the tetracyclic urazole 12c.Moreover, 6 reacts with PTAD considerably more sluggishly than 1b.

The Solvolysis of 3-Cyclooctatetraenylpropyl and 4-Cyclooctatetraenylbutyl p-Nitrobenzenesulfonates in 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoropropan-2-ol

The advantage of the use, compared to acetic acid, of 2,2,2-trifluoroethanol and 1,1,1,3,3,3-hexafluoropropan-2-ol for promoting ?-participation in the solvolytic reactions of 3-cyclooctatetraenylpropyl and 4-cyclooctatetraenylbutyl p-nitrobenzenesulfonates is demonstrated. 3-Cyclooctatetraenylpropyl p-nitrobenzenesulfonate solvolyses in buffered trifluoroethanol and hexafluoropropan-2-ol with ?-participation occurring to the extent of 73 and 99.5percent, respectively.The sole cyclized products is 2,9a-dihydro-1H-cyclopentacyclooctene. 4-Cyclooctatetraenylbutyl p-nitrobenzenesulfonate solvolyses in buffered trifluoroethanol and hexafluoropropan-2-ol with ?-participation occurring to the extent of 94 and 100percent, respectively.In buffered trifluoroethanol, the major cyclized products are two isomers of 10a-(2',2',2'-trifluoroethoxy)-1,2,3,4,4a,10a-hexahydrobenzocyclooctene (61.7percent) and 1,2,3,10a-tetrahydrobenzocyclooctene (28.9percent).The tetraene is almost the exclusive product (98.8percent) in buffered hexafluoropropan-2-ol.The probable involvement of substituted homotropylium ions and the role of ion-pairs in the solvolyses are discussed.