Chapter 7-Activating and Directive Effects of Silicon (p 355-430)

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1、TheChemistryofOrganicSiliconCompounds.Volume2EditedbyZviRappoportandYitzhakApeloigCopyright¶1998JohnWiley&Sons,Ltd.ISBN:0-471-96757-2CHAPTER7ActivatinganddirectiveeffectsofsiliconALANR.BASSINDALE,SIMONJ.GLYNNandPETERG.TAYLORDepartmentofChemistry,TheOpenUniversity,MiltonKeynes,MK76AA,

2、UKI.INTRODUCTION.....................................356II.ELECTRONICEFFECTSOFR3Si.........................356A.Introduction.......................................356B.InductiveEffects...................................356C.FieldEffects......................................357D.(pd)

3、Bonding...................................357E.Hyperconjugation...................................358III.THEMEASUREMENTANDINTERPRETATIONOFR3SiACTIVATINGANDDIRECTIVEPARAMETERS.........................359A.R3SiasaSubstituentinAromaticCompounds................359B.R3SiCH2asaSubstituenti

4、nAromaticCompounds.............361C.TheEffectofR3Sion˛-Silylcarbocations...................362D.TheEffectofR3SiCH2onAdjacentCarbocations..............364E.TheEffectofR3SiCH2CH2onAdjacentCarbocations...........375F.TheEffectofR3SiCH2CH2CH2onAdjacentCarbocations........380G.TheEffectof

5、R3Sion˛-Silylcarbanions....................381H.TheEffectofR3SiCH2onAdjacentCarbanions...............382IV.ACTIVATINGANDDIRECTIVEEFFECTSOFSILICONINELECTROPHILICAROMATICSUBSTITUTION...............382A.ReactionsofCompoundswithSiR3DirectlyBondedtotheAromaticRing.........................

6、...................382B.ElectrophilicAromaticSubstitutioninArCH2SiR3Compounds.....388V.ACTIVATINGANDDIRECTIVEEFFECTSINALIPHATICELECTROPHILICREACTIONS...........................388A.ReactionsofVinylsilanes..............................3881.Introduction.................................

7、....3882.Additiontovinylsilanes.............................3903.Substitutioninvinylsilanes...........................392B.ReactionsofAlkynylsilanes............................397C.ReactionsofAllylsilanes..............................398D.ReactionsofPropargylsilanes..................

8、.........411