the dakin rearrangement - hmvelms.org · the pinacol rearrangement is acid catalyzed dehydration of...
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Rearrangements
By
Dr Vandna Thakur
Assistant professor
Department of Chemistry
HMV
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SCHMIDT REACTION
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Introduction
Reaction of carboxylic acid with N3H in presence of H2SO4.
Yields both aliphatic and primary amines.
Reaction given by aldehydes, ketones, alcohols & alkenes too.
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MECHANISM
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EXAMPLES:1.
2.
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4.
3.
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5.
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Dakin Rearrangement
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The dakin reaction is an organic redox reaction in which an ortho or parahydroxylated phenyl aldehyde or ketone reacts with hydrogen peroxide in baseto form a benzenediol and a carboxylate .
The reaction works best if the aromatic aldehydes or ketones is electron rich.
Introduction
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MECHANISMThe mechanism of this reaction is related to
baeyer-villiger oxidation.the carbonyl compound
undergoes nucleophilic addition with
hydroperoxide anion to give tetrahedral
intermediate.
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EXAMPLES:
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The Pinacol Rearrangement is Acid
Catalyzed Dehydration of glycols which
converts the glycol into an aldehyde or a
ketone.
For Example:-
Introduction
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Mechanism of Pinacolic Transformation:-
This rearrangement is intramolecular rearrangement which is
confirmed by crossover experiment
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Migratory Aptitude:-The ease with which any particular group will undergo
nucleophillic 1,2-Shift is known as its migratory aptitude. All
groups do not migrate with equal ease.
Order of Decreasing migratory aptitude:-
It is been found that migratory
aptitude of phenyl group is
more than hydrogen which is
more than the alkyl group .
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Stereochemical And Conformational Factors:-
The most favourable Streochemistry for pinacolic
rearrangement is that the migrating group and the leaving group
are aligned in an anti- periplaner rearrangement easily in dilute
H2SO4 with migration of a methyl group whereas the trans
derivative undergoes rearrangement under similar conditions with
contraction of the ring.
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Examples Of Pinacol-Pinacolone
Rearrangement:-
1.
2.
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3.
4.
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5.
7.
6.
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8.
9.
10.
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CURTIUS REARRANGEMENT
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INTRODUCTION THE THERMAL/ PHOTOCHEMICAL REARRANGEMENT OF
ACYL AZIDES TO ISOCYANATES
ACYL AZIDES ARE USUALLY PREPARED EITHER BY REACT-
ION OF SODIUM AZIDE WITH A REACTIVE ACYLATING
AGENT OR BY A DIAZOTISATION OF AN ACYL HYDRAZIDE.
IT IS INTRAMOLECULAR REARRANGEMENT
THIS REACTION IS VERY GENERAL REACTION APPLICABLE
TO ALL CARBOXYLIC ACIDS-ALIPHATIC, ALICYCLIC,
HETROCYCLIC AS WELL AS AROMATIC
IT GIVES GOOD YIELD OF ISOCYANATE
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PREPERATION OF ACYL AZIDE
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REACTION
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MECHANISM
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Imp. Points about this rearrangement :-
In this rearrangement the key step is the thermal or
photochemical conversion of acyl azide to isocyanate .
This rearrangement is almost certainly concerted and does
not involve the intermediacy of a nitrene .
When curtius rearrangement is carried out in the presence of
vinyl monomers such as styrene ,it does not undergo
polymerisation .This rules out the formation of free radical ,
that is nitrene.
However ,there is evidence to support the existence of nitrene
when tertiary alkyl azides undergo curtius rearrangement to
form imines .
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Difference b\w curtius and hofmann
rearrangement :-
Both reactions gives isocyanates ,but isocyanates can be isolable in curtius but not in hoffmannrearrangement ,because base is present and the isocyanate can not survive .
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Stereochemistry of curtiusrearrangement :-
Studies of this rearrangemnt of optically active acyl azides in which the chiral carbon is directly bonded to this carbonyl group have shown that these reactions occur with retention of configuration .
Thus the chiral centre attach to the carbonyl group migrates to nitrogen with its electron but without inversion .
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example
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Beckmann rearrangement
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Introduction
The acid-catalysed conversion of ketoximes to amides is
known as Beckmann Rearrangement .A variety of protic
acids , Lewis acids , acid anhydrides and acyl halides can
cause the reaction to occur . The mechanism of reaction is
as shown :
.
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The role of catalysts like protic acids , Lewis
acids, acid anhydrides and acyl halides is to
convert the hydroxyl group into a better leaving
group. some acids (generally proton acids,
H2SO4,HCl and H3PO4) catalysed by simply
protonating the oxime. Other acids may esterify
the oximes.
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EXAMPLE:
The reaction is catalysed by arene sulphonyl chlorides
which react with oxime giving the corresponding sulphonate
R ArSO2Cl R
C=N-OH C=N-O-SO2-Ar
R R
R-C=N-R
O-SO2-Ar
O H2O
R-C –NH-R R-C=N-R
OSO2-Ar
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The oxime of ketone shows geometricalisomerism and it has two geometrical isomers ,syn and anti. When this reaction is carried outunder non-isomerising conditions , it is alwaysthe groups anti to the –OH that migrates.EXAMPLE:
NO2 PCl5 NO2
Cl C-C6H5 Cl C-NH-C6H5
N O
HO
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C6H5-C- - -Br (i) O
N-O NO2 (ii) H2 O Br- - CNHC6H5
NO2
NO2
O
Br C-C6H5 (i) P h-C-NH- -Br
N NO2 (ii) H2 O
O NO2
NO2
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HO-N H
CH3 H2S04 O N CH3
H3C ArSO2Cl H3C
Pyridine NH
H N H O
OH O
N-OH HCl Me3C-C-NH-
-C-CMe3 CH3COOH
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CH3 O
C=N-OH ArSO2Cl NH-C-CH3
Pyridine
H H
ArSO2Cl O
O Pyridine NH
N-OH
O H
N-OH H3PO4 N
N
N-OH O H
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Neber rearrangement
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Introduction REARRANGEMANT GIVEN BY KETOXIME
TOLUENESULPHONATES IN THE PRESENCE OF ALKOXIDESOF PYRIDINE TO GIVE α-AMINO KETONES.
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MECHANISM:- DEPROTONATION OF THE MIGRATION ORIGION.
THE CARBANION OBTANINED BY THE DEPROTONATION UNDERGOES INTERNAL DESPLACEMENT OF THE LEAVING GROUP TO FORM AN INTERMEDIATE AZIRINE.
AZIRINE ON HYDROLYSIS GIVES THE PRODUCT.
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SIMILAR REARRANGMENT IS GIVEN BY N, N-DICHLOROAMINES.
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• When both aldehyde and ketone are oxidised by per acid
known as baeyer villiger rearragement.
• This oxidation is the important reaction involing 1,2-
migration to the electro deficient oxygen.
•This oxidation is specially useful with ketone because it
convert them into carboxylic ester. Cyclic ketones
generate lactones .
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Salient Features
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C O
MMPP
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