Functional Groups:
Protecting group is stable under these conditions
Protecting group is moderately stable / might react
Protecting group is labile
Carbonyl Protecting Groups Stability
Dimethyl acetals | |||||||
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H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C |
Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 | |
Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 | |
Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH | |
Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 | |
Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 297-304, 724-727.
1,3-Dioxanes | 1,3-Dioxolanes | |||||||
H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C | ||
Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 | ||
Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 | ||
Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH | ||
Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 | ||
Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 308-322, 724-727.
1,3-Dithianes | 1,3-Dithiolanes | |||||||
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H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C |
Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 | ||
Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 | ||
Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH | ||
Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 | ||
Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 329-344, 724-727.
N,N-Dimethylhydrazone | |||||||
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H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C |
Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 | |
Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 | |
Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH | |
Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 | |
Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 350-352, 724-727.