Influence of Alkoxy Groups on Rates of Acetal Hydrolysis and Tosylate Solvolysis: Electrostatic Stabilization of Developing Oxocarbenium Ion Intermediates and Neighboring-Group Participation to Form Oxonium Ions

Journal of Organic Chemistry

Volumn 80, Issue 9, 2015, Pages 4470-4480

  Garcia, Angie ^a   Otte, Douglas A L ^a   Salamant, Walter A ^a,b   Sanzone, Jillian R ^a   Woerpel, K A ^a  

^a NEW YORK UNIVERSITY   (United States)

^b Bridgestone Americas Center for Research and Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROSTATICS; FUNCTIONAL GROUPS; IONS; SOLVENTS; STABILIZATION; SUBSTRATES; SULFUR COMPOUNDS;

ACETAL GROUPS; ALKOXY GROUP; CARBON ATOMS; ELECTROSTATIC STABILIZATION; FIVE-MEMBERED RINGS; OXOCARBENIUM; POSITIVE CHARGES; RATE ACCELERATION;

HYDROLYSIS;

ACETAL; CARBENE; FUNCTIONAL GROUP; HYDRONIUM ION; ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ALKOXYL RADICAL; CATION; FUSED HETEROCYCLIC RINGS; ION; TOLUENESULFONIC ACID DERIVATIVE;

ACCELERATION; ARTICLE; CHEMICAL REACTION KINETICS; HYDROLYSIS; MOLECULAR STABILITY; REACTION ANALYSIS; SOLVOLYSIS; STEREOSPECIFICITY; CHEMICAL STRUCTURE; CHEMISTRY; SOLUBILITY; STATIC ELECTRICITY; SYNTHESIS;

ACETALS; ALCOHOLS; BICYCLO COMPOUNDS, HETEROCYCLIC; HYDROLYSIS; IONS; MOLECULAR STRUCTURE; ONIUM COMPOUNDS; SOLUBILITY; STATIC ELECTRICITY; TOSYL COMPOUNDS;

EID: 84928920210     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00338     Document Type: Article

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