Matches in SemOpenAlex for { <https://semopenalex.org/work/W2029651198> ?p ?o ?g. }
- W2029651198 abstract "Selectivities that deviate from S(N)1 stereoelectronic models in the nucleophilic substitutions of tetrahydropyran acetals were investigated. When weak nucleophiles were employed, stereoselectivities conformed to known S(N)1 stereoelectronic models. In contrast, stereoselectivities in the substitutions of acetals with strong nucleophiles depended on reaction conditions. Erosions in selectivities were observed when strong nucleophiles were employed in the absence of coordinating counterions. These erosions in selectivities are attributed to rates of nucleophilic additions to oxocarbenium ion intermediates that approach the diffusion limit. When triflate counterions were present, however, S(N)2-like pathways became accessible with strong nucleophiles. In most cases examined, the major stereoisomers formed from reactions that proceeded through S(N)2-like pathways were opposite to the major stereoisomers formed from the analogous reactions that proceeded through S(N)1 pathways." @default.
- W2029651198 created "2016-06-24" @default.
- W2029651198 creator A5013113957 @default.
- W2029651198 creator A5030229929 @default.
- W2029651198 creator A5076723798 @default.
- W2029651198 date "2009-11-06" @default.
- W2029651198 modified "2023-10-16" @default.
- W2029651198 title "Correlations between nucleophilicities and selectivities in the substitutions of tetrahydropyran acetals." @default.
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- W2029651198 doi "https://doi.org/10.1021/jo901639b" @default.
- W2029651198 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4037909" @default.
- W2029651198 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19813702" @default.
- W2029651198 hasPublicationYear "2009" @default.
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