17.10 Reaction with Primary Amines: Imines
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Transcript of 17.10 Reaction with Primary Amines: Imines
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17.1017.10
Reaction with Primary Amines:Reaction with Primary Amines:
IminesImines
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Some reactions of aldehydes and ketones progressSome reactions of aldehydes and ketones progressbeyond the nucleophilic addition stagebeyond the nucleophilic addition stage
Acetal formationAcetal formation
Imine formationImine formation
Compounds related to iminesCompounds related to imines
EnaminesEnamines
The Wittig reactionThe Wittig reaction
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Some reactions of aldehydes and ketones progressSome reactions of aldehydes and ketones progressbeyond the nucleophilic addition stagebeyond the nucleophilic addition stage
Acetal formationAcetal formation
Imine formationImine formation
Compounds related to iminesCompounds related to imines
EnaminesEnamines
The Wittig reactionThe Wittig reaction
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CC OOHH22NN
RR
HHNN HH
RR
a carbinolaminea carbinolamine
NN
RR
CC + + HH22OO(imine)(imine)
CC OO••••
++•••• ••••••••
••••
••••
••••
Imine (Schiff's Base) FormationImine (Schiff's Base) Formation
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CHCH33NNHH22CHCH
OO
++
CH=CH=NNCHCH33 + + HH22OO
N-N-Benzylidenemethylamine (70%)Benzylidenemethylamine (70%)
ExampleExample
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CHCH33NNHH22CHCH
OO
++
CH=CH=NNCHCH33 + + HH22OO
N-N-Benzylidenemethylamine (70%)Benzylidenemethylamine (70%)
CHCH
OHOH
NNHHCHCH33
ExampleExample
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(CH(CH33))22CHCHCHCH22NNHH22OO ++
+ + HH22OO
N-N-Cyclohexylideneisobutylamine Cyclohexylideneisobutylamine (79%)(79%)
NNCHCH22CH(CHCH(CH33))22
ExampleExample
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(CH(CH33))22CHCHCHCH22NNHH22OO ++
+ + HH22OO
N-N-Cyclohexylideneisobutylamine Cyclohexylideneisobutylamine (79%)(79%)
NNCHCH22CH(CHCH(CH33))22
OHOH
NNHHCHCH22CH(CHCH(CH33))22
ExampleExample
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Some reactions of aldehydes and ketones progressSome reactions of aldehydes and ketones progressbeyond the nucleophilic addition stagebeyond the nucleophilic addition stage
Acetal formationAcetal formation
Imine formationImine formation
Compounds related to iminesCompounds related to imines
EnaminesEnamines
The Wittig reactionThe Wittig reaction
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Some reactions of aldehydes and ketones progressSome reactions of aldehydes and ketones progressbeyond the nucleophilic addition stagebeyond the nucleophilic addition stage
Acetal formationAcetal formation
Imine formationImine formation
Compounds related to iminesCompounds related to imines
EnaminesEnamines
The Wittig reactionThe Wittig reaction
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Reaction with Derivatives of AmmoniaReaction with Derivatives of Ammonia
HH22NN GG ++ RR22CC OO RR22CC NNGG ++ HH22OO
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Reaction with Derivatives of AmmoniaReaction with Derivatives of Ammonia
HH22NN GG ++ RR22CC OO RR22CC NNGG ++ HH22OO
HH22NN OHOH RR22CC NNOHOH
hydroxylaminehydroxylamine oximeoxime
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CHCH33(CH(CH22))55CHCH + H+ H22NNOHOH
OO
CHCH33(CH(CH22))55CHCH + H+ H22OO
NNOHOH
(81-93%)(81-93%)
ExampleExample
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Reaction with Derivatives of AmmoniaReaction with Derivatives of Ammonia
HH22NN GG ++ RR22CC OO RR22CC NNGG ++ HH22OO
HH22NN OHOH RR22CC NNOHOH
hydroxylaminehydroxylamine oximeoxime
HH22NN NHNH22 RR22CC NNNHNH22
hydrazinehydrazine hydrazonehydrazone
etc.etc.
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+ H+ H22NNNHNH22
+ H+ H22OO
(73%)(73%)
ExampleExample
OO
CC
NNNHNH22
CC
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CCHCCH33 + H+ H22NNNHNH
+ H+ H22OO
ExampleExample
OO
CCHCCH33
NNNHNH
phenylhydrazinephenylhydrazine
a phenylhydrazone (87-91%)a phenylhydrazone (87-91%)
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CHCH33(CH(CH22))99CCHCCH33
OO
HH22NNNHCNHNHCNH22
OO
HH22OOCHCH33(CH(CH22))99CCHCCH33
NNNHCNHNHCNH22
OO
++
++
ExampleExample
semicarbazidesemicarbazide
a semicarbazone (93%)a semicarbazone (93%)
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17.11Reaction with Secondary Amines:
Enamines
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Some reactions of aldehydes and ketones progressSome reactions of aldehydes and ketones progressbeyond the nucleophilic addition stagebeyond the nucleophilic addition stage
Acetal formationAcetal formation
Imine formationImine formation
Compounds related to iminesCompounds related to imines
EnaminesEnamines
The Wittig reactionThe Wittig reaction
![Page 20: 17.10 Reaction with Primary Amines: Imines](https://reader036.fdocuments.in/reader036/viewer/2022062423/56814a9d550346895db7ab42/html5/thumbnails/20.jpg)
Some reactions of aldehydes and ketones progressSome reactions of aldehydes and ketones progressbeyond the nucleophilic addition stagebeyond the nucleophilic addition stage
Acetal formationAcetal formation
Imine formationImine formation
Compounds related to iminesCompounds related to imines
EnaminesEnamines
The Wittig reactionThe Wittig reaction
![Page 21: 17.10 Reaction with Primary Amines: Imines](https://reader036.fdocuments.in/reader036/viewer/2022062423/56814a9d550346895db7ab42/html5/thumbnails/21.jpg)
RR22NNHH••••
++ HH22OO
(enamine)(enamine)
CC••••RR22NN
CC
Enamine FormationEnamine Formation
CC••••OORR22NN HH
HH CC
•••• ••••CC OO
••••
HH CC
••••
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++
(heat in benzene)(heat in benzene)
ExampleExample
OO
NNNNHH
(80-90%)(80-90%)
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++
(heat in benzene)(heat in benzene)
viavia
ExampleExample
OO
NNNNHH
OHOHN