Synthesis of Alkenes by Oxidative Decarboxylation of Carboxylic Acids Mechanistic Views The Organic Chemistry Notebook Series, A Didactical Approach, #6

REVISTA BOLIVIANA DE QUMICA (Rev.Bol.Quim.
)
Bolivian Journal of Chemistry
Received 09 09 2015
Accepted 09 10 2015
Bravo et Vila
Vol. 32, No.3, pp. 45-52, Jul./Ago. 2015

32(3) 45-52, Jul./Aug. 2015
Published 09 11 2015
.
SYNTHESIS OF ALKENES BY OXIDATIVE DECARBOXYLATION OF

CARBOXYLIC ACIDS; MECHANISTIC VIEWS; THE ORGANIC
CHEMISTRY NOTEBOOK SERIES, A DIDACTICAL APPROACH, N 6
Jos A. Bravo, Jos L. Vila*
Department of Chemistry, Laboratorio de Sntesis y Hemisntesis, Laboratorio de Fitoqumica, Instituto de
Investigaciones en Productos Naturales IIPN, Universidad Mayor de San Andrs UMSA, P.O. Box 303, Calle
Andrs Bello s/n, Ciudad Universitaria Cota Cota, Tel. 59122792238, La Paz, Bolivia. joselu62@hotmail.com,
jabravo@umsa.bo
Keywords: Organic Chemistry, oxidative decarboxylation, carboxylic acids, Alkenes,

Mechanisms of Reactions.
ABSTRACT
This is the sixth chapter in the series published by the same authors: The Organic Chemistry Notebook Series, a
Didactical Approach.
Here we offer the mechanistic views of the synthesis of alkenes by oxidative decarboxylation of carboxylic acids.
The aim of this series of studies is to help students to have a graphical view of organic synthesis reactions of diverse
nature. The oxidative decarboxylation of carboxylic acids is a useful method for generating alkenes. Here we propose
the mechanism and its discussion for the application of the method of decarboxylation of diacids lacking nearby
double bonds. Also, the route is explained mechanistically for the preparation of Dewar benzene. The thermal or
photolytic decomposition of di-t-butyl per-esters is described. The treatment of monocarboxylic acids to afford
alkenes in the presence of lead tetraacetate and copperII acetate is briefly discussed. The alkylation-decarboxylation
of aromatic acids is also explained. The oxidative decarboxylation of carboxylic acids can eventually conduct to the
obtaining of ketones instead of alkenes. We have used a series of reactions reviewed by W. Carruthers, and we have
proposed didactical and mechanistic views for them. This latest approach is included in the synthetic methods
reviewed by W. Carruthers with respect to the Formation of carbon-carbon double bonds. Spanish title: Sntesis de
alquenos por descarboxilacin de cidos carboxlicos; vistas mecansticas; De la serie: El cuaderno de notas de qumica orgnica, un enfoque
didctico, N6.
*Corresponding author: joselu62@hotmail.com

MECHANISTIC PROPOSALS AND DISCUSSION
Decarboxylation of vicinal diacids lacking nearby double bonds
As academics we are concerned with the didactical importance of covering the needs of debutant students in organic
synthesis. This is the sixth study in: The Organic Chemistry Notebook Series, a Didactical Approach [1-5]. The
method of decarboxylating carboxylic acids has proven to be useful [6]. Variations on the basic steps have been
introduced essentially for the improvement of the yields [6]. The aim is the generation of double C-C bonds starting
with vicinal dicarboxylic acids and subsequent decarboxylation, as schematically viewed in Fig. 1 [6,7].
CO2H
2CO2 + 2H+ + 2e
CO2H
O
H
O
O H
O C O
+
+ H +
:-C O H
O
O H
O
O
O C O + H- + H+
2H+ + 2 e-
Figure 1. Vicinal dicarboxylic acid as starting material for generating double C-C bonds; reviewed by W. Carruthers [5]
Downloadable from: Revista Boliviana
45
de Qumica. Volumen 32 N3. Ao 2015
http://www.bolivianchemistryjournal.org, http://www.scribd.com/bolivianjournalofchemistry
REVISTA BOLIVIANA DE QUMICA (Rev.Bol.Quim.)

Received 09 09 2015
Vol. 32, No.3, pp. 45-52, Jul./Ago. 2015

32(3) 45-52, Jul./Aug. 2015
Accepted 09 10 2015
Bravo et Vila
The treatment with lead tetraacetate in boiling benzene can be improved with the presence of oxygen becoming thus
applicable for vicinal dicarboxylic acids lacking nearby double bonds [6] (Fig. 2).
CO2H
Pb(OCOCH3)4, O2
(76%)
pyridine, 670C
CO2H
Figure 2. Synthesis of 1,4-cyclohexadiene by decarboxylation 4,5-ciclohexendicarboxylic acid, reviewed by W. Carruthers [6]
The mechanism is seen in Fig. 3. In step 1, lead acetate pulls off a proton from one of the carboxylic acid residues of
the substrate to form a carboxylate residue. What follows is the immediate excision of the bonding of the substituent
carboxylate. This electronic movement evokes somehow the Diels Alder mechanism with respect to the formation of
the new double bond. The contrast is the rupture of both sigma bonds instead of the transformation of two double
into single bonds in Diels Alder. However, indeed, this is not a pericyclic reaction. Besides cyclohexenone, CO2 and
carbanionic carboxylic acid evolve from this fragmentation. The acid-base interaction between the acetic acid
formed from the lead tetraacetate and the carbanionic carboxylic acid gives formic acid and tetraacetate is
regenerated. In step 2, tetraacetate pulls off a proton from formic acid provoking decarboxylation (generation of
CO2) and acetic acid plus 4 hydrides. In step 2, two of the four acetic acid equivalents ionize and generate two
acetate and two proton equivalents. These two proton equivalents plus two from the four hydride equivalents of step
2 generate 4 protons and 4 e- due to oxidation of hydride in step 3. In step 4, PbIV (Pb4+) is reduced to Pbo thanks to
the previous oxidation step that provided four e-. In step 5, two of the four proton equiv generated in step 3 interact
with two acetate residues to generate 2 acetic acid equiv. Step 6 is the covalence formation between 2H+ and 2Hgenerating H2.
4 O
O
O
4
4CH3COO
C
H
Pb
O
4 C
O
4
O
-
+ 4CH3COO
4+
, O2
+4: C
+ [4CH3COOH] + 4H
H + 4CH3COOH
= 4CO + [2CH COOH

2
+
+ 2(CH3COO +H )] + 4H
2H+ + 2e- then
+
since H + H
2H+ + 2H-
4H+ + 4e-
Pb4+ + 4e-
Pbo
2H+ + 2CH3COO-
2CH3COOH
2H+
2H2
2H-
Final balanced equation:

O
O
4
O
O
H
H
[CH3COO-]4PbIV
+ 4CH3COOH + 2H2 + Pbo + 8CO2
Figure 3. Synthesis of 1,4-cyclohexadiene by oxidative decarboxylation of 4,5-ciclohexendicarboxylic acid; mechanistic views
An interesting procedure with good yields is the obtaining of dienes by electrolysis of the dicarboxylic acid in
pyridine solution with trimethylamine added. The reaction goes on in mild conditions, and the method is appropriate
for preparing highly strained unsaturated small and bridged ring compounds [6]. As an example lets mention the
preparation of Dewar benzene from bicyclo[2,2,0]hex-2-en-5,6-dicarboxylic acid, Fig. 4 [6].
COOH
COOH
electrolysis
pyridine
(CH3)3N
Figure 4. Dewar benzene obtained by electrolysis in pyridine solution with trimethylamine from bicyclo[2,2,0]hex-2-en-5,6dicarboxylic acid. Reviewed by W. Carruthers [6]
46

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32(3) 45-52, Jul./Aug. 2015
Accepted 09 10 2015
Bravo et Vila
In the first step an acid reaction occurs with the liberation of a proton from one of the acid residues of
bicyclo[2,2,0]hex-2-en-5,6-dicarboxylic acid. Triethylamine serves as temporary base to accommodate this proton
but soon after the proton is partially reduce by 1e- to .H. Also, decarboxylation occurs with the first carboxylate
residue to form the alkene and expel the second carboxylic acid residue under the form of carbanion. In the second
step, the carbanionic carboxylic acid frees its proton which neutralizes the carbanion to afford formiate. Formiate
expels a hydride and generates an equivalent of carbon dioxide. In the third step the hydride oxidizes to give a proton
and two electrons, one of which generates a second .H species. The .H species overlap each other and form gaseous
hydrogen. This step regenerates the electron employed in the electrolytic method under review. See Fig. 5 for
mechanistic proposal.
O
N(C2H5)3
H
O
H
OO
O
+ HN+(C2H5)3 + 1e
O
O
H.
H +
:C
O-
+ H+ + H.
.
+ H
+ N(C2H5)3
O
-
O-
:C
O
O-
O-
+H
+ H + H.
C
O
1eH+ + 2e-
H. + 1e- + H.
.
+ H
Final balanced equation:

O
H
O
O
+ 1e
H
O
O
H
O
O
H
O
H2 + 1e
2CO2
+ H2
2CO2
+ 1e
+ H2
Figure 5. Dewar benzene obtained by electrolysis in pyridine solution with trimethylamine from bicyclo[2,2,0]hex-2-en-5,6dicarboxylic acid. Mechanism
An easy and useful method, done under mild conditions, and activated under thermal or radiation conditions to
provoke photolytic decomposition, uses t-butyl peresters, obtained at its turn from diacid chlorides and t-butyl
hydroperoxide, Fig. 6 [6].
This photolysis reaction is applicable for synthesizing thermally unstable alkenes [6]. The vicinal dicarboxylic
acids employed in this reaction can be obtained by Diels Alder reaction [6]. An alternative is the photosensitised
addition of maleic anhydride to dienes or alkenes [6].
CO2OC4H9-t
CO2OC4H9-t
h
0
C6H6, 25 C
Figure 6. Photolytic decomposition of t-butyl peresters under thermal or radiation conditions to afford unstable alkenes.
Reviewed by W. Carruthers [6]
The obtaining of the t-butyl peresters is effected by nucleophilic substitution using diacid chloride as starting
substrate and t-butylhydroperoxide as nucleophile. The outer oxygen of one equivalent of the two tbutylhydroperoxide equivalents acts as nucleophile over one of the acid chloride function of the bicyclo-compound.
This forms a mono-t-butylperester derivative protonated. The second step is the substitution on the second acid
chloride extreme of the bicyclo-compound to afford a di-t-butylperester. What follows is the irradiation of the di-tbutylperester which provokes homolytic rupture of the weakest bonding in the substrate, namely the peroxide bridge.
This fact generates two single radicals (t-butoxy) and a double radical (di-carboxylate radical). This extremely
reactive species (the double radical), collapses into another double radical (proto-alkene) and two carbonic
anhydride residues. The two single radicals (t-butoxy) prefer to couple each other to generate a t-butoxyperoxide
molecule. See Fig. 7 for this mechanism.
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32(3) 45-52, Jul./Aug. 2015
Accepted 09 10 2015
Bravo et Vila
Obtaining of di-t-butylperesters
O
O
Cl
Cl
Diacid chloryde
O H
..
O O
H
Cl
+ H-O-OC4H9-t
C4H9-t
Cl
O+ O C H -t
4 9
+ClCl
t-butylhydroperoxide
O
O
O O C H -t
4 9
+HCl
Cl
O
O O C H -t
4 9
H
Cl
O
.. O
O
O
C4H9-t
O O C H -t
4 9
2HCl
+HCl
C4H9-t
O
O O C H -t
4 9
O O C H -t
4 9
O
O O C H -t
4 9
O O C H -t
4 9
O O C H -t
4 9
+ClO+ O
C4H9-t
H
Decarboxylation
O
O O
O O C H -t
4 9
O O C H -t
4 9
O
O O C H -t
4 9
O O C H -t
4 9
+ 2CO2 +
O O C H -t
4 9
O O C H -t
4 9
t-C 4H9-O-O-C4H9-t
Figure 7. Photolytic decomposition of t-butyl peresters under thermal or radiation conditions to afford unstable alkenes.
Mechanistic views
The oxidative decarboxylation of mono-carboxylic acids is a related reaction to the previously described reactions,
and this is effected under treatment with lead-tetraacetate [6]. The development of the reaction depends on the
structure of the acid giving poor yields and mixture of products, this, under normal conditions [6]. However, with the
addition of catalytic amounts of copperII acetate the increasing of the yields of alkenes synthesized is significant [6].
The reaction is applied to primary and secondary carboxylic acids, either under photolysis, or under thermolysis, in
benzene at its boiling point [6]. For example, nonanoic acid can be transformed into 1-octene in high yields and
cyclobutanecarboxylic acid affords cyclobutene in 77 % yield. A mechanism by free radicals has been proposed by
authors [6]. See Fig. 8.
CH3(CH2)7CO2H + Pb(OAc)4
Cu(OCOCH3)2
h C6H6 30C
CO2H
CH3(CH2)5CH=CH2
quantitative
Pb(OCOCH3)4
Cu(OCOCH3)2
(77%)
C6H6 reflux
RCO2PbIII
R
CuII
CuI + RCO2PbIV
R + CO2 + PbII
alkene + H+ + CuI
CuII + RCO2PbIII, etc
Figure 8. Decarboxylation of mono-carboxylic acids with lead tetraacetate; free radicals mechanism. Reviewed by W.
Carruthers [6]
The mechanism is shown in Fig. 9. The acetates of lead and copper dissociate to give PbIV and CuII. Under the
limited information offered by the review, we proposed a mechanism including radical formation. The mechanism is
composed of two steps: initiation step and chain propagation. The initiation step (that is not mentioned in the review
[6]) is assumed here as addition of a catalytic amount of H2 to the reacting mixture and subsequent photolysis giving
rise to the radical H. and its oxidation to afford an initial electron to be employed in the chain-propagation during the
first reduction of PbIV to PbIII. During the loop, this electron is provided by oxidation of CuI to CuII. The chain
propagation includes a first step of carboxylic acid dissociation to acetate and H+ followed by reduction of PbIV to
48

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32(3) 45-52, Jul./Aug. 2015
Accepted 09 10 2015
Bravo et Vila
III
II
III
Pb with the electron provided soon after by the oxidation of Cu to Cu . The acetate and the Pb they form an
adduct; this adduct absorbs radiation (h) and gives rise to R., CO2 and PbII. The alklyl R. becomes an alkene and an
H radical. This H radical is oxidized to H+ to provide the electron to reduce CuII into CuI. The complementary part of
the chain propagation is the oxidation of PbII into PbIV and CuI into CuII and the generation of H2. After this, the
cycle reinitiates at the stage of the dissociation of the carboxylic acid. This mechanistic proposal is highly limited
and restrained by certain lack of information which is unavailable in the review [6], and could be improved after
proper consultations with the correct bibliographic source. Let us remark with respect to Fig. 8 and 9, that those
reactions inside the blue and red square in Fig. 8, are mechanistically explained in squares of the corresponding color
in Fig. 9.
Pb(AcO)4
PbIV + 4AcO-
Cu(AcO)2
CuII + 2AcO-
Initiation step
h
H2
H + H
+
1e- + H
st
OH
only 1 time
O-
O
PbIV + 1e-
nd
from2 time on
PbIII
O-
PbIII +
+
+ H
PbIII
O
Pb
III
Chain propagation
CH2
PbII
CH
H
CH
CH
H
+ H
CH2
CH
H
H
H+ + 1e-
H
CuII + 1e+
CH2
CH2 +
CuI
CH2
CuII
I
+
+ H + Cu
PbII
PbIV + 2e-
CuI
CuII + 1e-
H+ + 1e-
H+ + 1e-
H2
+ H
`
Figure 9. Decarboxylation of mono-carboxylic acids with lead tetraacetate; free radicals mechanism. Mechanistic views
As an example of the applications of this reaction lets cite the alkylation-decarboxylation of aromatic acids. Fig. 10.
CH3
CH3
CH3
Pb(OCOCH3)4
(1) Li, NH3
CO2H
O
(2)
Cu(OCOCH3)2
Br
CO2H
C6H6, 350C
Figure 10. Alkylation-decarboxylation of aromatic acids. Reviewed by W. Carruthers [6]
49

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32(3) 45-52, Jul./Aug. 2015
Accepted 09 10 2015
Bravo et Vila
The lithium and ammonia employed provoke somehow delocalization of one of the aromatic systems until locating
the negative charge over the carbonyl oxygen of the aromatic acid. The direct alkylation occurs when the carbanion
attacks the alkyl bromide in a SN2 manner [6]. The furan derivative, rosefuran can be obtained following the
oxidative radical process of Fig. 10 and 11 [6].
Initiation step
Li++ 1e-
Li
NH3 + H2O
NH4+ + OH-
Li+ + OH-
LiOH
NH4+
NH3 + H+
H
H+ + 1e-
Li+ + OH
LiOH
H
O
LiOH + H
O+
H
O- Li+
H2O
+ H2O
Li
H+
1e- +
H
OH- + H+
O
-
O Li
O+
H
H
Br
O+
H
H
O-
H
H
PbIV + 1e-
PbIII
from2 time on
st
(only 1 time)
O+
O
Pb
O-
O+
PbIII
H
O+
O
PbIII
H
+
C O
C
C
+
H
C
H
H
PbII
CO2 + PbII
PbIV + 2e-
..C ....O
.C O.
..
C
H C C
.
..
+
C O
C
C
H
C
.
..
PbII
..
..
C O
C
H C C
H
H
O
H+
nd
III
H
O
O
H
H
Br
O+
2e
C
H C C
H
H+ + 1e-
H
CuII + 1e-
..C ....O
CuI
..
..
C
H C C
+
H+
C O
C
H C C
=
O
O+
C
H
CuII
I
+ Cu
Chain propagation
H
CuI
CuII + 1e-
Figure 11. Alkylation-decarboxylation of aromatic acids. Mechanistic views.

50

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32(3) 45-52, Jul./Aug. 2015
Accepted 09 10 2015
Bravo et Vila
These two last mechanisms (Fig. 9 and 11) although presenting some species stoichiometrically unjustified (H and
AcO-), give at least a global idea of the movement of species as well as the oxidation-reducing processes.
A carboxylic acid can be converted into a ketone instead of an alkene following oxidative decarboxylation.
Carbon loss is verified during the process [6]. The acid converted in a dianion suffers sulphenylation under dimethyl
disulphide [6]. The sulphenylated acid reacts with N-chlorosuccinimide and gives a diacetal with loss of carbon
anhydride adding sodium bicarbonate [6]. The diacetal goes a hydrolysis to afford the ketone at 0oC [6]. The acid can
be synthesized from cyclohexadiene and acrylic acid; this last is equivalent to the ketene in this homologue of the
Diels Alder reaction [6]. See Fig. 12.
Cl
R
R'
(1) 2LiN(iso-C3H7)2
CO2H
(2) CH3SSCH3
SCH3
R'
CO2H
OC2H5
R'
OC2H5
H3O+
R'
S+CH3
N-chlorosuccinimide
C2H5OH, NaHCO3
R'
C O
C2H5OH
S+CH3
R'
CO2H
+ CO2
Figure 12. Conversion of a carboxylic acid into ketone by decarboxylation. Reviewed by W. Carruthers [6]
Another example is shown in Fig. 12 with the decarboxylation of bicyclo[2.2.2]hept-5-ene-2-carboxylic acid into
(1R,4R)-bicyclo[2.2.2]hept-5-en-2-one [6]. The mechanistic views corresponding to Fig. 12 are exposed in Fig. 13 and
14.
RH
R'
i-pr
Li+:N-
+
O H
+
R Li
i-pr
..-
R'
i-pr
H
i-pr
O- Li
HN
R'
S O
H3C
CH3S
'R
..'R
CH3S
..
O H
++ Li SCH3
Cl
O
O-
Cl
CH3
Cl
CH3+S
'R
O
O-
..
H
O
N-chlorosuccinimide
'R
S+
Cl+
CH3
'R
R
O
C
O
..
C2H5O+
..
CH3
C2H5O
OC2H5
Cl+
+ H Cl
C2H5O+
H
CH3
S+
C2H5O
ClC2H5O+
Cl-
R'R
+ HSCH3
OC2H5
HOC2H5
HOC2H5
R'R
Cl-
'R
R
RR'
R'R
+ H2O
OC2H5
C2H5O
ClO+H2 + C H OH
2 5
RR'
C2H5O+
O
H
'R
O
C2H5OH
Figure 13. Conversion of a carboxylic acid into a ketone instead of an alkene following oxidative decarboxylation. Mechanistic
views.
Figure 13 shows the substrate under attack by a strong base, Li+N-(i-pr)2. The proton in presents an extra acidic
character due to the carbonyl group. This proton interacts with the base Li+N-(i-pr)2 to form a carbanion. The
51

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32(3) 45-52, Jul./Aug. 2015
Accepted 09 10 2015
Bravo et Vila
negative charge (two electrons) over the carbanion, delocalize to form the alkenes double bond and thus to dispatch
the mobile electrons of carbonyl to the carbonyls oxygen to generate an alcoxy group. The allylalcoxy (stabilized
by the cation Li+) moves its electrons as nucleophile over dimethyl disulphide breaking the inter-sulfur linkage, all
provoked by the reformation of the carbonyl group by localization of the negative excessive charge on oxygen. The
-methyl thioether carboxylic acid, after the introduction of the S-group in , presents now acidity enough to interact
with the N-chlorosuccinimide. The N-chlorosuccinimide protonated frees a chloride (Cl-) by means of an nucleophilic
attack from the sulfur from the -methyl thioether carboxylic acid. The chlorinated thioether carboxylate residue frees
a chloride by decarboxylation and formation of the double bond between carbon and sulfur. A double nucleophilic
addition of ethanol with configuration inversion occurs with this substrate to generate an ethyl-acetal which by means
of protonation of the first ethanol residue and subsequent separation as alcohol by hydrolysis and elimination of the
second protonated ethanol, finally conducts to the ketone product. Figure 14 is a similar mechanism to figure 13.
assuming
a defined
stereochemistry
at C-2
O
O H
CO2H
+ Li+:N-
i-pr
O
O H
i-pr
Li+
..
bicyclo[2.2.2]hept-5-ene-2-carboxylic acid
O
Cl
+
O H
CH3
N-chlorosuccinimide
+
+ Cl N
H
O
O
S
H 3C
Li+ -
CH3
CH3
O
O+
H3C
CH3
HOC2H5
OC2H5
O+C2H5
HOC2H5
Cl-
OH
O
O
H
+
Li+
O
CH3
H 3C
..
O
OH
S
S
H 3C
ClCl-
H 3C
S+
ClH
Cl
OC2H5 + HSCH3 ;
+
O C2H5
+ CO2 + Cl
+ H N
S
H 3C
ClH
OC2H5 + H2O
+
O C2H5
Cl+
O 2H + HOC2H5
OC2H5
O H
+ HOC2H5 + HCl
Cl- O+C H
O
2 5
H
(1R,4R)-bicyclo[2.2.2]hept-5-en-2-one
Figure 14. Conversion of bicyclo[2.2.2]hept-5-ene-2-carboxylic acid into (1R,4R)-bicyclo[2.2.2]hept-5-en-2-one instead of an

alkene following oxidative decarboxylation. Mechanistic views.
ACKNOWLEDGEMENTS
The authors express their gratitude to Prof. Eduardo Palenque from the Department of Physics, Universidad Mayor
de San Andrs, for his bibliographic support.
REFERENCES
1.
2.
3.
4.
5.
6.
7.
Bravo, J. 2005, Rev. Bol. Quim., 23, 1. (http://www.bolivianchemistryjournal.org, 2005).

Bravo, J.A., Mollinedo, P., Pearrieta, J.M., Vila, J.L. 2013, Rev. Bol. Quim., 30, 24 (http://www.bolivianchemistryjournal.org,
2013).
Bravo, J.A., Vila, J.L. 2014, Rev. Bol. Quim., 31, 61 (http://www.bolivianchemistryjournal.org, 2014).
Bravo, J.A., Vila, J.L. 2015, Rev. Bol. Quim., 32, 15 (http://www.bolivianchemistryjournal.org, 2015).
Vila, J.L., Bravo, J.A. 2015, Rev. Bol. Quim., 32, 37 (http://www.bolivianchemistryjournal.org, 2015).
Carruthers, W. Some Modern Methods of Organic Synthesis, Cambridge University Press, 3rd ed., 1987, Worcester, U.K., pp.
159-162.
Sheldon, R.A., Kochi, J.K. 1972, Organic Reactions, 19, 279.
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REVISTA BOLIVIANA DE QUMICA (Rev.Bol.Quim.

Vol. 32, No.3, pp. 45-52, Jul./Ago. 2015