10.6A Mechanism of hydroboration More substituted Less substituted Hydroboration H3CHc=CH2+H—B3 H3cHc丰cHz THE Propene H—B—H Boron hydride H π Complex H3C—c--c—H H3C—c—c—H H---B HB—H Four center transition state H CH3CHCH2 CH3CH=CH2 -(CH3 CH2) BH (CH3 CH,CH)3B Hydroboration Hydroboration Tripropylborane 三丙基硼
10.6A Mechanism of hydroboration H3C C H C H H H B H H Four center transition state H3C C H C H H H B H H H3CHC CH2 + H B H H Hydroboration Boron hydride Propene THF More substituted Less substituted H3CHC CH2 H B H H Complex CH3CH=CH2 (CH3CH2CH2 ) 2BH CH3CH=CH2 (CH3CH2CH2 ) 3B Tripropylborane 三 丙 基 硼 Hydroboration Hydroboration
10.6b The stereochemistry of hydroboration More substituted H Syn addition CH H—B THE Less substituted Boron hydride H—B—H anti-Markovnikov 硼氢化反应的特点;1顺式加成。2反马加成
10.6B The stereochemistry of hydroboration + H B H H Hydroboration Boron hydride THF More substituted Less substituted CH3 CH3 H H H B H Syn addition anti-Markovnikov 硼氢化反应的特点；1.顺式加成。2.反马加成
10.7 Alcohols from alkenes through hydroboration oxidation. BH/THF HbO, NaoH 3 CH3 CH=CH2 (CH3 CH, CH2)3B CHrCHChboH Hydroboration Tripropylborane 1-Propanol 三丙基硼 More substituted H Syn addition H—B THE deboration Less substituted Boron hydride H H anti-Markovnikov H,Oz, NaoH
10.7 Alcohols from alkenes through hydroborationoxidation (CH3CH2CH2 ) 3B Tripropylborane 三 丙 基 硼 Hydroboration 3 CH3CH=CH2 BH3 / THF H2O2 , NaOH CH3CH2CH2OH 1-Propanol + H B H H Hydroboration Boron hydride THF More substituted Less substituted CH3 CH3 H H H B H Syn addition anti-Markovnikov H CH3 OH H H2O2 , NaOH
1. BH3/THF CH3 CH2 CH,CH2CH=CH2 CH3 CH2 CH,CH, CH,CHOH 2. H,O, NaOH 1-Hexene I-Hexanol Anti-Mar's rule CH3,CH2CH2CH=CH H,O HSO CH3CH2CH2CH2 CHCH3 1-Hexene 2-Hexanol OH Follow Mar's rule CH3 CH- 1. BH,/THF CH3C=CHCH3 2. H202, NaOH CH3CHCHCH3 2-Methyl-2-butene OH 3-Methy1-2-butanol Anti-Mar's rule
2. H2O2 , NaOH CH3CH2CH2CH2CH=CH2 1. BH3 / THF CH3CH2CH2CH2CH2CH2OH 1-Hexene 1-Hexanol Anti-Mar's Rule CH3 CH2 CH2 CH2 CH=CH2 H2O, H2 SO4 CH3 CH2 CH2 CH2 CHCH3 2-Hexanol 1-Hexene OH Follow Mar's Rule 2. H2 O2 , NaOH CH3 C=CHCH3 1. BH3 / THF 3-Methyl-2-butanol 2-Methyl-2-butene Anti-Mar's Rule CH3 CH3 CHCHCH3 CH3 OH