Side reactionmolecularrearrangementCHsHCH3HCICH3-C-C-CH3-> CH3—C-CH2CH3H OHCICH3CH3CH3HBrCH3-C-CH2OHC-CHCH3+ CH3-C-CH-CH3CH3-1CH3Br
Side reaction—molecular rearrangement CH3 C C CH3 CH3 H H OH CH3 C CH2 CH3 CH3 Cl HCl CH3 C CH2OH CH3 CH3 HBr CH3 C CH2CH3 CH3 Br CH3 C CH CH3 CH3 +
(2) reaction with phosphorus halides3 CHsOH + PI3 —→ 3 CH3CH2I + H3PO3mechanism:1I>CH3CH20-P:+ IP_ICH3CH2OH + HI1H IHOCH3CH2O P: +I+ P→ ICH2CH3 +T1H-HOPI22ＲIRITR-O
(2) reaction with phosphorus halides mechanism： 3 C2 H5 OH + PI 3 3 CH3 CH2 I + H3 PO3 CH3 CH2 OH + P I I I CH3 CH2 O P H I I + I CH3 CH2 O P + I H I I ICH2 CH3 + P I I HO R O H P I I -HOPI 2 R RI -I
(3)Reaction with sulfinyl chloride醚、ROH + SOCl2RCl + SO24 + HCI△mechanism:00R0R00. YoR-CISCStS+CHH'CIHCIH'R'CiCIR'CICIHR氯代亚硫酸酯OY0R0ORHR'CIH紧密离子对RC-CI+SO2H
mechanism： (3) Reaction with sulfinyl chloride ROH + SOCl 2 RCl + SO2 + HCl 醚 S O Cl Cl C R O H H R' C R O H S O R Cl ' C Cl R H R' + SO2 - Cl + S O C Cl l C R O H H R' C R O H R S O Cl Cl ' 氯代亚硫酸酯 R C H R' O S O Cl 紧密离子对
Svi(Substitution Nucleophilic internal)mechanism:RCIHPOHNCIHCI
SNi(Substitution Nucleophilic internal) mechanism： C R O H S O R Cl ' + N S O C R H R O N Cl + N HCl HN Cl
R0R福-HCI+SO2+CIHR'CIRRR0C-HCCI=OHRRSO2+
Cl C R O H S O R Cl ' Cl C H R R + SO2 + Cl Cl S O C R H R O N Cl C H R R + N + SO2