Three-Electron SN2 Reactions of Arylcyclopropane Cation Radicals. 2. Steric and Electronic Effects of Substitution1

Autor:	M.W. McKenney, Han Zuilhof, Joseph P. Dinnocenzo, D. R. Lieberman, T. R. Simpson
Rok vydání:	1997
Předmět:	Steric effects Regioselectivity General Chemistry Photochemistry Biochemistry Catalysis Cyclopropane chemistry.chemical_compound Colloid and Surface Chemistry chemistry Nucleophile Kinetic isotope effect Nucleophilic substitution Electronic effect SN2 reaction
Zdroj:	Journal of the American Chemical Society. 119:994-1004
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja963112s
Popis:	The nucleophilic substitution reactions on substituted arylcyclopropane cation radicals were studied by a combination of methods including product studies, time-resolved laser flash photolysis, kinetic isotope effects, and quantum chemical calculations. The reactions were found to proceed stereospecifically with inversion of configuration, with high regioselectivity for nucleophilic attack at the more substituted carbon atom, and with very small steric effects. Electronic effects on the nucleophilic substitution regiochemistry and the rate constants were found to be substantial for substituents on the cyclopropane moiety and on the aryl ring.
Databáze:	OpenAIRE
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