704-02-9

Upstream product

• 114095-89-5 11-methylenepentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecane-8-spiro-3'-diazirine 
• 87830-51-1 11-methylenepentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecan-8-one 
• 1076-13-7 (1α,4α,4aα,5α,8α,8aα)-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene 
• 101418-79-5 C₁₃H₁₄O₂ 
• 114130-42-6 C₁₉H₁₉N₂O₂S^(1-)*Na⁽¹⁺⁾ 
• 3212-28-0 1,8,9,10,11,11-Hexachlor-hexacyclo[6.2.1.1^3.6.0^2.7.0^4.10.0^5.9]dodecan 

Downstream Products

• 60606-96-4 2a,3,3a,5a,6,6a,6b,6c-Octahydro-dicyclopenta[cd,gh]pentalene 
• 60606-96-4 acs-Tetracyclo<7.2.1.0^4,11.0^6,10>dodeca-2,7-dien 

Relevant academic research and scientific papers

Variations in Mechanism for Photoinduced Valence Isomerization of an Electron-Donor Nonconjugated Diene

Photoisomerization of 1,4,4a,5,8,8a-hexahydro-1,4,5,8-endo,endo-dimethanonaphthalene (3) has been studied in detail.Rearrangement to the cage photoisomer 4 occurs on direct irradiation or with triplet sensitizers with quantum efficiency as high as 1.0.Irradiation in the presence of electron acceptors whose fluorescence is quenched by 3 also results in cage formation.Quantum yields approach 1.0 for donor-acceptor sensitization in a nonpolar solvent.For this reaction, a mechanism is proposed that involves excitation transfer within an exciplex of sensitizer and 3 and partitioning of locally excited 3 at a biradicaloid geometry.Quantum efficiencies exceed unity for rearrangement sensitized by electron acceptors in polar media.A chain mechanism is proposed that involves radical-cation intermediates obtained through electron transfer from 3.Irradiation of ground-state (charge-transfer) complexes of 3 and fumaronitrile or diethyl 1,2-dicyanofumarate also results in valence isomerization with quantum yields that are dependent on solvent polarity and excitation wavelength.The options available for photosensitization of 3 and a related diene, norbornadiene, are discussed.

Photolysis of 11-methylenepentacyclo-[5.4.0.02,6.03,10.0 5,9]undecan-8-spiro-3′-diazirine. Medium dependent reaction

11-Methylenepentacyclo[5.4.0.02,6.03,10.0 5,9]undecan-8-spiro-3′-diazirine (1) has been synthesized and its photochemical decomposition in different media has been investigated. Irradiation of N2-purged benzene solution of diazirine 1 produced a mixture of four azine-isomers 7a-d. However, photolysis of 1 in pentane gave a mixture of hydrocarbons 6 as the main insertion products and traces of 1,3-bishomopentaprismane (5). The photolytic decomposition of 1 in N2-matrix at -196 °C proved the formation of diazo-compound 8, which upon warm-up gave traces of 1,3-bishomopentaprismane (5).

1,7-Methanohomopentaprismane: A Propellane

The intramolecular cycloaddition of 11-methylene-8-pentacyclo2,6.03,10.05,9>undecanylidene to the olefinic bond leads to 1,7-methanohomopentaprismane, a highly elusive propellane, which spontaneously abstracts two hydrogen atoms from its environment, yielding 1,3-bishomopentaprismane.