FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2316778499> ?p ?o ?g. }

• W2316778499 endingPage "9136" @default.
• W2316778499 startingPage "9127" @default.
• W2316778499 abstract "The chemistry of (S)-methyl xanthates derived from xylo- and ribo-furanose derivatives in the presence of the stannyl radical is investigated. Xanthate derived from β-xylo-furanose affords exclusively a deoxygenated product; whereas, under the same reaction conditions, the α-ribo-furanose xanthate derivative produces quantitatively a hemithioacetal compound. We reasoned that in the case of the β-xylo-furanose derivative, a favorable β-oxygen effect in the Barton–McCombie deoxygenation reaction is operating where, according to theoretical calculations, unusual molecular orbital interactions (and not strain, as previously proposed) are present. These orbital interactions involve the SOMO (intermediary generated from the stannyl radical addition) with the σ* orbital of the bond undergoing cleavage and this with the two C–O antibonding orbitals anti oriented. Such molecular orbital interactions are not present in the α-ribo-furanose; therefore, the β-scission is highly delayed, and due to the reversibly nature of the stannyl radical addition, the ribo-furanose xanthate is forced to take an alternative route: the homolytic substitution (SH2) of the sulfide sulfur by stannyl radical. This radical addition gives the alkoxythiocarbonyl radical, which is trapped by Bu3SnH before the elimination of carbonyl sulfide; subsequently, radical stannyl addition followed by radical reduction produces the hemithioacetal." @default.
• W2316778499 created "2016-06-24" @default.
• W2316778499 creator A5015829668 @default.
• W2316778499 creator A5020090317 @default.
• W2316778499 creator A5021776971 @default.
• W2316778499 creator A5021945780 @default.
• W2316778499 creator A5033485143 @default.
• W2316778499 creator A5062661363 @default.
• W2316778499 creator A5091484441 @default.
• W2316778499 date "2013-09-09" @default.
• W2316778499 modified "2023-10-13" @default.
• W2316778499 title "β-Oxygen Effect in the Barton–McCombie Deoxygenation Reaction: Further Experimental and Theoretical Findings" @default.
• W2316778499 cites W1507717639 @default.
• W2316778499 cites W1873649893 @default.
• W2316778499 cites W1964567477 @default.
• W2316778499 cites W1966596550 @default.
• W2316778499 cites W1981317123 @default.
• W2316778499 cites W1982356449 @default.
• W2316778499 cites W1984599229 @default.
• W2316778499 cites W1993383767 @default.
• W2316778499 cites W2002194503 @default.
• W2316778499 cites W2007794567 @default.
• W2316778499 cites W2015753123 @default.
• W2316778499 cites W2023271753 @default.
• W2316778499 cites W2032719166 @default.
• W2316778499 cites W2036601571 @default.
• W2316778499 cites W2038767330 @default.
• W2316778499 cites W2054461976 @default.
• W2316778499 cites W2068573006 @default.
• W2316778499 cites W2069285941 @default.
• W2316778499 cites W2069643261 @default.
• W2316778499 cites W2070644362 @default.
• W2316778499 cites W2081066007 @default.
• W2316778499 cites W2085966856 @default.
• W2316778499 cites W2089654491 @default.
• W2316778499 cites W2090577680 @default.
• W2316778499 cites W2127976054 @default.
• W2316778499 cites W2139916893 @default.
• W2316778499 cites W2949448678 @default.
• W2316778499 cites W2951285257 @default.
• W2316778499 cites W2951554629 @default.
• W2316778499 cites W3005388311 @default.
• W2316778499 doi "https://doi.org/10.1021/jo4012943" @default.
• W2316778499 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23987098" @default.
• W2316778499 hasPublicationYear "2013" @default.
• W2316778499 type Work @default.
• W2316778499 sameAs 2316778499 @default.
• W2316778499 citedByCount "8" @default.
• W2316778499 countsByYear W23167784992017 @default.
• W2316778499 countsByYear W23167784992018 @default.
• W2316778499 countsByYear W23167784992019 @default.
• W2316778499 countsByYear W23167784992022 @default.
• W2316778499 countsByYear W23167784992023 @default.
• W2316778499 crossrefType "journal-article" @default.
• W2316778499 hasAuthorship W2316778499A5015829668 @default.
• W2316778499 hasAuthorship W2316778499A5020090317 @default.
• W2316778499 hasAuthorship W2316778499A5021776971 @default.
• W2316778499 hasAuthorship W2316778499A5021945780 @default.
• W2316778499 hasAuthorship W2316778499A5033485143 @default.
• W2316778499 hasAuthorship W2316778499A5062661363 @default.
• W2316778499 hasAuthorship W2316778499A5091484441 @default.
• W2316778499 hasConcept C121332964 @default.
• W2316778499 hasConcept C139066938 @default.
• W2316778499 hasConcept C139358910 @default.
• W2316778499 hasConcept C147120987 @default.
• W2316778499 hasConcept C147597530 @default.
• W2316778499 hasConcept C155647269 @default.
• W2316778499 hasConcept C161790260 @default.
• W2316778499 hasConcept C173985810 @default.
• W2316778499 hasConcept C175689099 @default.
• W2316778499 hasConcept C178790620 @default.
• W2316778499 hasConcept C181199279 @default.
• W2316778499 hasConcept C185592680 @default.
• W2316778499 hasConcept C189394030 @default.
• W2316778499 hasConcept C2776821766 @default.
• W2316778499 hasConcept C2779778602 @default.
• W2316778499 hasConcept C2780378348 @default.
• W2316778499 hasConcept C2780636463 @default.
• W2316778499 hasConcept C3044715 @default.
• W2316778499 hasConcept C32909587 @default.
• W2316778499 hasConcept C62520636 @default.
• W2316778499 hasConcept C71240020 @default.
• W2316778499 hasConcept C75473681 @default.
• W2316778499 hasConcept C95269574 @default.
• W2316778499 hasConceptScore W2316778499C121332964 @default.
• W2316778499 hasConceptScore W2316778499C139066938 @default.
• W2316778499 hasConceptScore W2316778499C139358910 @default.
• W2316778499 hasConceptScore W2316778499C147120987 @default.
• W2316778499 hasConceptScore W2316778499C147597530 @default.
• W2316778499 hasConceptScore W2316778499C155647269 @default.
• W2316778499 hasConceptScore W2316778499C161790260 @default.
• W2316778499 hasConceptScore W2316778499C173985810 @default.
• W2316778499 hasConceptScore W2316778499C175689099 @default.
• W2316778499 hasConceptScore W2316778499C178790620 @default.
• W2316778499 hasConceptScore W2316778499C181199279 @default.
• W2316778499 hasConceptScore W2316778499C185592680 @default.
• W2316778499 hasConceptScore W2316778499C189394030 @default.
• W2316778499 hasConceptScore W2316778499C2776821766 @default.

• next