An Investigation of Inverted Phenyl:methyl Substituent Effects in the Solvolysis of Substituted Endo-7-methylene-2-norbornyl Tosylates |
Common terms and phrases
1,1 diphenylethylene 2-norbornyl tosylate 2-position 7-methylene-2-norbornyl 7-norbornenone 74 mmol acetolysis acetone acetone:water alkyl and aryl Amer anti isomer aryl aryl substituent benzene benzhydrylidene Benzylidene bicyclo 2.2.1 bicyclo 2.2 cation CH₂ODNB Chem chloride chromatography concentrated cyclopropyl cyclopropyl carbinyl delocalized di-aryl substituted di-methyl substituted di-phenyl diene difference dimethyl sulfoxide dioxane distilled to give double bond ethanol ether/petroleum ether Ethylidene bicyclo ground state stabilization H OTS heat of hydrogenation heats of solution heptan-2-ol heptene homoallylic hydrolysis ibid inverted substituent effects kcal/mol ketone kinetic lithium aluminum hydride methyl substitution Methylene mmol mono mono-substituted nmr CDC13 norbornyl norbornyl system pentane phenyl substitution phosphonate phosphorane rate of solvolysis ratio recrystallized refluxed resonance resulting Schleyer sodium hydride sodium hydride 57 solvent solvolysis steric stirred styrene substituted system substrates temperature tetrahydrofuran thin film tosylate tosylate was prepared unsaturated values Wittig Reaction Xanthydrylidene ΔΕ