FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2017189154> ?p ?o ?g. }

• W2017189154 endingPage "748" @default.
• W2017189154 startingPage "741" @default.
• W2017189154 abstract "The mechanism and regioselectivity of gold(I)-catalyzed synthesis of highly substituted furans based on 1-(1-alkynyl)cyclopropyl ketones with nucleophiles have been investigated using density functional theory calculations done at the BH and HLYP/6-31G(d, p) (SDD for Au) level of theory. Solvent effects on these reactions have been explored by calculations that included a polarizable continuum model (PCM) for the solvent (dichloromethane). Our calculations suggest that the first step of the cycle is the cyclization of the carbonyl oxygen onto the triple bond to form a new and stable five-membered resonance structure of an oxonium ion and a carbocation intermediate. Furthermore, the seven-membered carbocation intermediate proposed by Zhang and Schmalz was found and characterized as a transition structure on the potential energy surface. The attack of the carbonyl oxygen to the gold-coordinated alkynes results in the formation of a resonance structure intermediate, which upon subsequent trapping with alcohols followed by migration of a hydrogen atom results in the formation of the final products and regeneration of the catalyst. The key reaction step is the attack of the oxygen atom of the CH3OH on the C−C σ bond of the cyclopropane moiety to yield new organogold intermediates through formation of a C−O bond and cleavage of a C−C bond. The cleavage of the C−C bond is strongly favored kinetically in the case of the C1−C2 bond and required only 19.8 kcal/mol of energy, while the activation energy for cleavage of the C1−C3 bond was found to be 31.8 kcal/mol and indicates that the ring-opening cycloisomerization for cyclopropyl ketones has high regioselectivity. Our computational results are consistent with the experimental observations of Zhang and Schmalz for the gold(I)-catalyzed synthesis of highly substituted furans based on 1-(1-alkynyl)cyclopropyl ketones with nucleophiles." @default.
• W2017189154 created "2016-06-24" @default.
• W2017189154 creator A5002170896 @default.
• W2017189154 creator A5004415040 @default.
• W2017189154 creator A5021086726 @default.
• W2017189154 creator A5027185848 @default.
• W2017189154 date "2009-01-07" @default.
• W2017189154 modified "2023-09-30" @default.
• W2017189154 title "DFT Study on the Mechanism and Regioselectivity of Gold(I)-Catalyzed Synthesis of Highly Substituted Furans Based on 1-(1-Alkynyl)cyclopropyl Ketones with Nucleophiles" @default.
• W2017189154 cites W1529984049 @default.
• W2017189154 cites W1963688013 @default.
• W2017189154 cites W1963737263 @default.
• W2017189154 cites W1981451973 @default.
• W2017189154 cites W1982356449 @default.
• W2017189154 cites W1989905363 @default.
• W2017189154 cites W1993729590 @default.
• W2017189154 cites W1995794402 @default.
• W2017189154 cites W2004776657 @default.
• W2017189154 cites W2011180004 @default.
• W2017189154 cites W2014727876 @default.
• W2017189154 cites W2014767176 @default.
• W2017189154 cites W2015723183 @default.
• W2017189154 cites W2019263180 @default.
• W2017189154 cites W2019786890 @default.
• W2017189154 cites W2021322395 @default.
• W2017189154 cites W2023271753 @default.
• W2017189154 cites W2025002140 @default.
• W2017189154 cites W2025925059 @default.
• W2017189154 cites W2031586681 @default.
• W2017189154 cites W2032214615 @default.
• W2017189154 cites W2035311414 @default.
• W2017189154 cites W2039411511 @default.
• W2017189154 cites W2047212413 @default.
• W2017189154 cites W2050155564 @default.
• W2017189154 cites W2051716884 @default.
• W2017189154 cites W2064300335 @default.
• W2017189154 cites W2067011309 @default.
• W2017189154 cites W2068599812 @default.
• W2017189154 cites W2082023915 @default.
• W2017189154 cites W2086548206 @default.
• W2017189154 cites W2093053427 @default.
• W2017189154 cites W2094227165 @default.
• W2017189154 cites W2094797643 @default.
• W2017189154 cites W2100030276 @default.
• W2017189154 cites W2107504045 @default.
• W2017189154 cites W2107728155 @default.
• W2017189154 cites W2107743975 @default.
• W2017189154 cites W2109297253 @default.
• W2017189154 cites W2120477715 @default.
• W2017189154 cites W2127915043 @default.
• W2017189154 cites W2130243797 @default.
• W2017189154 cites W2145759636 @default.
• W2017189154 cites W2155160318 @default.
• W2017189154 cites W2157811548 @default.
• W2017189154 cites W2170651437 @default.
• W2017189154 cites W2324978857 @default.
• W2017189154 cites W2949686510 @default.
• W2017189154 cites W2949937291 @default.
• W2017189154 cites W2950851381 @default.
• W2017189154 cites W2951107552 @default.
• W2017189154 cites W2951631018 @default.
• W2017189154 cites W2951803313 @default.
• W2017189154 cites W2951839660 @default.
• W2017189154 cites W4233173389 @default.
• W2017189154 cites W4247851196 @default.
• W2017189154 cites W4377077185 @default.
• W2017189154 doi "https://doi.org/10.1021/om800751u" @default.
• W2017189154 hasPublicationYear "2009" @default.
• W2017189154 type Work @default.
• W2017189154 sameAs 2017189154 @default.
• W2017189154 citedByCount "37" @default.
• W2017189154 countsByYear W20171891542012 @default.
• W2017189154 countsByYear W20171891542013 @default.
• W2017189154 countsByYear W20171891542014 @default.
• W2017189154 countsByYear W20171891542015 @default.
• W2017189154 countsByYear W20171891542016 @default.
• W2017189154 countsByYear W20171891542017 @default.
• W2017189154 countsByYear W20171891542018 @default.
• W2017189154 countsByYear W20171891542020 @default.
• W2017189154 crossrefType "journal-article" @default.
• W2017189154 hasAuthorship W2017189154A5002170896 @default.
• W2017189154 hasAuthorship W2017189154A5004415040 @default.
• W2017189154 hasAuthorship W2017189154A5021086726 @default.
• W2017189154 hasAuthorship W2017189154A5027185848 @default.
• W2017189154 hasConcept C109057382 @default.
• W2017189154 hasConcept C132439834 @default.
• W2017189154 hasConcept C145148216 @default.
• W2017189154 hasConcept C147597530 @default.
• W2017189154 hasConcept C152365726 @default.
• W2017189154 hasConcept C155647269 @default.
• W2017189154 hasConcept C161790260 @default.
• W2017189154 hasConcept C178386823 @default.
• W2017189154 hasConcept C178790620 @default.
• W2017189154 hasConcept C178907741 @default.
• W2017189154 hasConcept C185592680 @default.
• W2017189154 hasConcept C196099240 @default.
• W2017189154 hasConcept C2776122248 @default.
• W2017189154 hasConcept C2776568683 @default.

• next