I Nucleophilic Rearrangement 1 Wagner-Meerwein rearrangement Carbon cation rearrangement H CH -C-CH,OH-Ark CH3-C-CH,OH2 HO CH3-—CH2CH3 CH3-C--CH2 CH3-f-CH2CH3 CH cH 3 CH3C=CHCH3 CH3
II Nucleophilic Rearrangement 1 Wagner-Meerwein rearrangement ( Carbon cation rearrangement ) H + CH3 C CH3 CH3 CH2 OH H2 O CH3 C CH3 CH3 CH2 OH2 CH3 C CH3 CH3 CH2 H + Cl - CH3 C CH3 CH2CH3 CH3C=CHCH3 CH3 CH3 C CH3 CH2CH3 Cl
Cl C c OH
Cl Cl - Cl - Cl OH H + + +
CH CHS-「HH3scH--cHH3→ CH3 Br CH3 C--「HCH→ Product CH3 CH3 Stable cation CHPh SNI 3 CH-C CH CHPh 关 CH CHPh CH2 Br CH 3 CH3 CH3 Stable cation Product CH3O /> > >>CH2=CH >R2C->R2CH->CH3->H-
CH3 C CH3 CH3 CHCH3 Br SN1 CH3 C CH3 CH3 CHCH3 CH3 C CH3 CHCH3 CH3 Product CH3 C CH3 CH3 CHPh CH SN1 3 C CH3 CH3 CHPh Br Product CH3 C CH3 CHPh CH3 CH3O ＞ ＞ Cl ＞ CH2 =CH ＞ R3 C ＞ R2CH ＞CH3 ＞H Stable cation Stable cation
HNO CHa-C-Choh CH CH 2 CH3 CH3-C-CH2CH3-20 OH F-CH2CH3 CH3 CHNH HNO 2 H,OHOH CH HO Ht
CH3 C CH3 CH3 CH2 OH N2 HNO2 CH3 C CH3 CH3 CH2 CH3 C CH3 CH2CH3 H + H2O CH3 C CH3 CH2CH3 OH CH2NH2 NH2 HNO2 N2 CH2 + + H + H2 O H + CH OH 2OH CH2
CHNH HO HNO2 CHOH H+ 2 32 H H H2o OH 2 58% NH HNO HO Dt HO H CH,=CHCH2OH
N2 HNO2 CH2 NH2 H + H2 O H + CH2 + CH2 OH 32% + H2 O H + OH 58% H + 2% NH2 HNO2 N2 + + H + H2O H + H2O CH2 =CHCH2OH