FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2051903043> ?p ?o ?g. }

• W2051903043 endingPage "740" @default.
• W2051903043 startingPage "733" @default.
• W2051903043 abstract "The BF3-catalyzed ring-opening reaction of variously endo/exo m- and p-substituted diarylhomobenzoquinone epoxides proceeded through a transannular SE2-Ar cyclization of endo-aryl groups to give the tricyclic diketo-alcohols and cyclohexadienone spiro-linked tricyclic diketo-alcohols. Kinetics of these reactions has been investigated in CDCl3 at 30 °C in order to elucidate the possible remote π-aryl participation. The rates were significantly increased with increasing electron-donating ability of the endo-aryl substituents X (kp-MeO/kp-CF3 = 8200) but only negligibly influenced by the distal exo-aryl substituents Y (kp-MeO/kp-CF3 = 2.1). For the endo-X substituted series, an excellent linear free energy relationship, log krelendo = −2.49σipso − 1.62σortho − 0.108 (R2 = 0.98, n = 8), was attained using two modified site-dependent substituent parameters σipso (using σp+ for p-X and σm for m-X) and σortho (using σm for p-X and σp+ for m-X). This means that the dihapto(η2) π-coordination occurs in the π-aryl participation, with the ipso π-electron donation contributing 1.6 times more effectively than the ortho one. On the other hand, the distal exo-Y substituted series gave an acceptable Yukawa−Tsuno equation with small polar and resonance contributions; log krelexo = −0.912(σ0 + 0.237Δσ̅R+) (R2 = 0.96, n = 8). These kinetic substituent effects were compared with those of the acid-catalyzed π-aryl assisted transannular SE2-Ar cyclization of the cyclobutene-fused diarylhomobenzoquinones. It was found that the geometrical characteristics of the vacant oxirane Walsh orbital and the cyclobutene antibonding orbital play a crucial role in the topological features of η2 π-aryl participation." @default.
• W2051903043 created "2016-06-24" @default.
• W2051903043 creator A5010296653 @default.
• W2051903043 creator A5017595263 @default.
• W2051903043 creator A5053411423 @default.
• W2051903043 creator A5065280369 @default.
• W2051903043 date "2009-12-21" @default.
• W2051903043 modified "2023-10-05" @default.
• W2051903043 title "Kinetic Evidence for Dihapto (η²) π-Aryl Participation in Acid-Catalyzed Ring Opening of Diarylhomobenzoquinone Epoxides" @default.
• W2051903043 cites W1963842634 @default.
• W2051903043 cites W1983280228 @default.
• W2051903043 cites W1995484011 @default.
• W2051903043 cites W1997574605 @default.
• W2051903043 cites W1999631659 @default.
• W2051903043 cites W2007986139 @default.
• W2051903043 cites W2020168329 @default.
• W2051903043 cites W2021874606 @default.
• W2051903043 cites W2022762542 @default.
• W2051903043 cites W2027512421 @default.
• W2051903043 cites W2031549829 @default.
• W2051903043 cites W2033442972 @default.
• W2051903043 cites W2036624416 @default.
• W2051903043 cites W2044257095 @default.
• W2051903043 cites W2047066956 @default.
• W2051903043 cites W2047318406 @default.
• W2051903043 cites W2052003622 @default.
• W2051903043 cites W2054894273 @default.
• W2051903043 cites W2062917731 @default.
• W2051903043 cites W2064594390 @default.
• W2051903043 cites W2065364332 @default.
• W2051903043 cites W2066325743 @default.
• W2051903043 cites W2071415803 @default.
• W2051903043 cites W2072634686 @default.
• W2051903043 cites W2074930747 @default.
• W2051903043 cites W2077156484 @default.
• W2051903043 cites W2086240644 @default.
• W2051903043 cites W2089160922 @default.
• W2051903043 cites W2090391132 @default.
• W2051903043 cites W2093367613 @default.
• W2051903043 cites W2095072830 @default.
• W2051903043 cites W2122405999 @default.
• W2051903043 cites W2152278650 @default.
• W2051903043 cites W2153839113 @default.
• W2051903043 cites W2315641439 @default.
• W2051903043 cites W2335337813 @default.
• W2051903043 cites W2502246907 @default.
• W2051903043 cites W2520561313 @default.
• W2051903043 cites W2950589839 @default.
• W2051903043 cites W2951638561 @default.
• W2051903043 cites W2952549985 @default.
• W2051903043 cites W3004995130 @default.
• W2051903043 cites W3005365945 @default.
• W2051903043 cites W585575871 @default.
• W2051903043 cites W1966571399 @default.
• W2051903043 doi "https://doi.org/10.1021/jo902179x" @default.
• W2051903043 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/20025262" @default.
• W2051903043 hasPublicationYear "2009" @default.
• W2051903043 type Work @default.
• W2051903043 sameAs 2051903043 @default.
• W2051903043 citedByCount "7" @default.
• W2051903043 countsByYear W20519030432012 @default.
• W2051903043 countsByYear W20519030432014 @default.
• W2051903043 countsByYear W20519030432022 @default.
• W2051903043 crossrefType "journal-article" @default.
• W2051903043 hasAuthorship W2051903043A5010296653 @default.
• W2051903043 hasAuthorship W2051903043A5017595263 @default.
• W2051903043 hasAuthorship W2051903043A5053411423 @default.
• W2051903043 hasAuthorship W2051903043A5065280369 @default.
• W2051903043 hasConcept C121332964 @default.
• W2051903043 hasConcept C135889238 @default.
• W2051903043 hasConcept C14158195 @default.
• W2051903043 hasConcept C155647269 @default.
• W2051903043 hasConcept C161790260 @default.
• W2051903043 hasConcept C178790620 @default.
• W2051903043 hasConcept C185592680 @default.
• W2051903043 hasConcept C2776011334 @default.
• W2051903043 hasConcept C2778689049 @default.
• W2051903043 hasConcept C2780263894 @default.
• W2051903043 hasConcept C2780378348 @default.
• W2051903043 hasConcept C2781076698 @default.
• W2051903043 hasConcept C32909587 @default.
• W2051903043 hasConcept C62520636 @default.
• W2051903043 hasConcept C71240020 @default.
• W2051903043 hasConceptScore W2051903043C121332964 @default.
• W2051903043 hasConceptScore W2051903043C135889238 @default.
• W2051903043 hasConceptScore W2051903043C14158195 @default.
• W2051903043 hasConceptScore W2051903043C155647269 @default.
• W2051903043 hasConceptScore W2051903043C161790260 @default.
• W2051903043 hasConceptScore W2051903043C178790620 @default.
• W2051903043 hasConceptScore W2051903043C185592680 @default.
• W2051903043 hasConceptScore W2051903043C2776011334 @default.
• W2051903043 hasConceptScore W2051903043C2778689049 @default.
• W2051903043 hasConceptScore W2051903043C2780263894 @default.
• W2051903043 hasConceptScore W2051903043C2780378348 @default.
• W2051903043 hasConceptScore W2051903043C2781076698 @default.
• W2051903043 hasConceptScore W2051903043C32909587 @default.
• W2051903043 hasConceptScore W2051903043C62520636 @default.
• W2051903043 hasConceptScore W2051903043C71240020 @default.

• next