877-06-5

Usage

Uses

Used in Organic Synthesis:
7-TERT-BUTOXYNORBORNADIENE is used as a building block in organic synthesis for the creation of a variety of other chemical compounds, contributing to the development of new products and materials.
Used in Material Science:
In the field of material science, 7-TERT-BUTOXYNORBORNADIENE is used as a component in the development of new materials, potentially leading to innovative applications and advancements in this area.
Used in Coordination Chemistry:
7-TERT-BUTOXYNORBORNADIENE also serves as a ligand in coordination chemistry, playing a crucial role in the formation and properties of coordination compounds.

InChI:InChI=1/C11H16O/c1-11(2,3)12-10-8-4-5-9(10)7-6-8/h4-10H,1-3H3

Upstream product

• 53943-71-8 3-t-Butoxyquadricyclane 
• 109-65-9 1-bromo-butane 
• 2404-35-5 cycloheptyl bromide 
• 1120-57-6 chlorocyclobutane 
• 931-51-1 cyclohexylmagnesiumchloride 
• 1068-55-9 isopropylmagnesium chloride 
• 15366-08-2 s-butylmagnesium chloride 
• 23719-80-4 cyclopropylmagnesium bromide 
• 32916-51-1 cyclopentylmagnesium chloride 
• 614-45-9 tert-Butyl peroxybenzoate 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 

Downstream Products

• 1609-39-8 7-chlorobicyclo<2.2.1>hepta-2,5-diene 
• 3391-07-9 7-tert.-Butoxy-norbornan 
• 136708-48-0 7-t-butoxy-4-phenylsulfonyl-4-azatetracyclo<3.3.0.0^2,8.0^3,6>octane 
• 71886-41-4 7-(4-methoxyphenyl)bicyclo<2.2.1>heptadiene 
• 136708-49-1 7-t-butoxy-4-(4'-chlorophenylsulfonyl)-4-azatetracyclo<3.3.0.0^2,8.0^3,6>octane 
• 71901-60-5 7-(4-methylphenyl)bicyclo<2.2.1>heptadiene 
• 136708-51-5 syn-8-t-butoxy-2-(4'-nitrophenylsulfonyl)2-azabicyclo<3.2.1>octa-3,6-diene 
• 136708-50-4 7-t-butoxy-4-(4'-nitrophenylsulfonyl)-4-azatetracyclo<3.3.0.0^2,8.0^3,6>octane 
• 40156-12-5 7-phenylnorbornadiene 
• 74964-58-2 7-(4-fluorophenyl)bicyclo<2.2.1>heptadiene 
• 78074-62-1 ((1R,2R,6S,7R)-10-tert-Butoxy-3-oxa-4-aza-tricyclo[5.2.1.0^2,6]deca-4,8-dien-5-yl)-phenyl-methanone 
• 78074-62-1 ((1S,2R,6S,7S)-10-tert-Butoxy-3-oxa-4-aza-tricyclo[5.2.1.0^2,6]deca-4,8-dien-5-yl)-phenyl-methanone 
• 54163-87-0 endo-3,3-diphenyltricyclo<3.2.1.0^2,4>oct-6-ene 
• 71901-61-6 7-o-Tolylnorbornadien 

Relevant academic research and scientific papers

Gas-phase pyrolysis mechanism and kinetics of 3-t-butoxyquadricyclane

The gas-phase pyrolysis of 3-t-butoxyquadricyclane [1] was investigated over the temperature range 511 -542 K at one atm in helium. The initial pyrolysis step is the isomerization of 3-t-butoxyquadricyclane to 7-t-butoxynorbornadiene (Ea = 38.49 ± 0.85 kcal/mole, log A = 15.44 ± 0.35). 7-t-butoxynorbornadiene exhibits a single unimolecular reaction pathway which produces a mixture of t-butoxycycloheptatrienes (Ea = 38.44 ± 0.63 kcal/mole, log A = 15.05 ± 0.26). This two-step mechanism affords fewer reactions than unsubstituted quadricyclane in the gas phase and could be useful for its reduced sooting potential.

C3-Symmetric Tricyclo[2.2.1.02,6]heptane-3,5,7-triol

A straightforward access to a hitherto unknown C3-symmetric tricyclic triol both in racemic and enantiopure forms has been developed. Treatment of 7-tert-butoxynorbornadiene with peroxycarboxylic acids provided mixtures of C1- and C3-symmetric 3,5,7-triacyloxynortricyclenes via transannular π-cyclization and replacement of the tert-butoxy group. By refluxing in formic acid, the C1-symmetric esters were converted to the C3-symmetric formate. Hydrolysis gave diastereoisomeric triols, which were separated by recrystallization. Enantiomer resolution via diastereoisomeric tri(O-methylmandelates) delivered the target triols on a gram scale. The pure enantiomers are useful as core units of dopants for liquid crystals.

Tandem Ring-Opening–Ring-Closing Metathesis for Functional Metathesis Catalysts

Use of a tandem ring-opening–ring-closing metathesis (RORCM) strategy for the synthesis of functional metathesis catalysts is reported. Ring opening of 7-substituted norbornenes and subsequent ring-closing metathesis forming a thermodynamically stable 6-membered ring lead to a very efficient synthesis of new catalysts from commercially available Grubbs’ catalysts. Hydroxy functionalized Grubbs’ first- as well as third-generation catalysts have been synthesized. Mechanistic studies have been performed to elucidate the order of attack of the olefinic bonds. This strategy was also used to synthesize the ruthenium methylidene complex.

Photodissociation Dynamics of Cyclopropenylidene, c-C3H2

In this joint experimental and theoretical study we characterize the complete dynamical "life cycle" associated with the photoexcitation of the singlet carbene cyclopropenylidene to the lowest lying optically bright excited electronic state: from the initial creation of an excited-state wavepacket to the ultimate fragmentation of the molecule on the vibrationally hot ground electronic state. Cyclopropenylidene is prepared in this work using an improved synthetic pathway for the preparation of the precursor quadricyclane, thereby greatly simplifying the assignment of the molecular origin of the measured photofragments. The excitation process and subsequent non-adiabatic dynamics have been previously investigated employing time-resolved photoelectron spectroscopy and are now complemented with high-level ab initio trajectory simulations that elucidate the specific vibronic relaxation pathways. Lastly, the fragmentation channels accessed by the molecule following internal conversion are probed using velocity map imaging (VMI) so that the identity of the fragmentation products and their corresponding energy distributions can be definitively assigned.

Synthesis of anti-2,7-disubstituted norbornadienes

Synthesis of a variety of anti-2,7-disubstituted norborna- dienes was achieved by palladium- and iron-catalyzed cross- coupling reactions of the anti-tert-butoxynorbornadien-2-yl triflate. While the palladium-catalyzed coupling reactions could only genera

Ruthenium(II)-catalyzed [2+2] cycloadditions of anti 7-substituted norbornenes

The ruthenium(II)-catalyzed [2+2] cycloadditions of anti 7-substituted norbornenes with an alkyne were investigated. The cycloadditions were found to proceed with a high degree of stereoselectivity, giving only the exo stereoisomers in moderate to good yields using an improved protocol. Comparative rate studies between a variety of anti 7-substituted norbornenes and an alkyne revealed that the reactivity of the alkene component decreases dramatically as the alkene becomes more electron deficient. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.