Reaction of tri- and tetrasubstituted alkenes with the low-temperature oxidizing system aluminum terf-butylate-terf-butyl hydroperoxide

Article abstract of DOI:10.1023/A:1012357318443

The system consisting of aluminum tert-butylate and tert-butyl hydroperoxide under mild conditions (20°C) oxidizes tri- and tetrasubstituted ethylenes containing at least one α-methyl group. The reaction proceeds via formation of tertiary allylic hydroperoxides and their subsequent transformations into unsaturated alcohols and epoxy alcohols, and also into carbonyl compounds. The presence of the latter products suggests degradation of the carbon skeleton of alkenes.

Full text of DOI:10.1023/A:1012357318443

Russian Journal of General Chemistry, Vol. 71, No. 5, 2001, pp. 736 741. Translated from Zhurnal Obshchei Khimii, Vol. 71, No. 5, 2001,
pp. 785 790.
Original Russian Text Copyright
2001 by Martynova, Stepovik, Dodonov.
Reaction of Tri- and Tetrasubstituted Alkenes
with the Low-Temperature Oxidizing System
Aluminum tert-Butylate tert-Butyl Hydroperoxide
I. M. Martynova, L. P. Stepovik, and V. A. Dodonov
Lobachevskii State University, Nizhni Novgorod, Russia
Received November 16, 1999
Abstract The system consisting of aluminum tert-butylate and tert-butyl hydroperoxide under mild condi-
tions (20 C) oxidizes tri- and tetrasubstituted ethylenes containing at least one -methyl group. The reaction
proceeds via formation of tertiary allylic hydroperoxides and their subsequent transformations into unsaturated
alcohols and epoxy alcohols, and also into carbonyl compounds. The presence of the latter products suggests
degradation of the carbon skeleton of alkenes.
The system consisting of aluminum tert-butylate
I and tert-butyl hydroperoxide II is an oxidant of
alkanes, alkylarenes [1], as well as of their oxygen-
containing derivatives: alcohols, aldehydes, ketones
[2], ethers [3], and esters [4]. Reaction of the com-
ponents I and II of the system leads to the evolution
of oxygen [1 4] through the intermediate formation of
di(tert-butoxy)-tert-butylperoxyaluminum and alu-
minum-containing trioxide [scheme (1)].
known that the stability and the energy of formation
.
1
of the benzyl radical [E(PhCH2 ) 85 kcal mol ] are
.
close to those of the allyl radical [E(CH2=CH=CH2 )
1
89 kcal mol ] [5]. The latter can be formed in the
course of oxidation of -C H bonds in alkenes.
In this work we studied the reactions of tetra-
and trisubstituted alkenes (2,3-dimethyl-2-butene III,
2-methyl-2-butene IV, 1,1-diphenylpropene V, 1,1-di-
phenyl-2-methylpropene VI) with the oxidizing sys-
tem I II. We expected oxidation of the methyl group
with the intermediate formation of allylic radicals and
epoxidation of the double bond. According to pub-
lished data [6], peroxy compounds of boron, silicon,
and gallium oxidize alkenes to the corresponding
epoxides. Note that hydroperoxide II reacts with the
double bond in alkenes only in the presence of transi-
tion metal (vanadium, molybdenum, chromium, etc.)
derivatives [7].
(t-BuO)3Al + t-BuOOH
(t-BuO)2AlOOBu-t
(t-BuO)2AlOOOBu-t
t-BuOH
t-BuOOH
(t-BuO)2Al O O Bu-t
t-BuO O H
(1)
(t-BuO)3Al + O2
Radical oxidation of methyl and methylene bonds
with this system depending on the structure of ali-
phatic and alkylaromatic hydrocarbons leads in the
first stage to introduction of oxo, hydroxy [1, 2, 4],
and hydroperoxy groups [1, 3]. The resulting func-
tional derivatives are involved in subsequent reactions
with di(tert-butoxy)-tert-butylperoxyaluminum as well
as with the system I II. In most cases their oxidation
is accompanied by the cleavage of carbon carbon
bonds in the starting substrate. Note that, in spite of
the fairly wide range of the studied compounds, direct
oxidation of methyl group was observed only in tol-
uene. It was noted previously that the carbon hy-
drogen bonds of the benzene ring do not react with
the above system [1]. The oxidation of substrates
proceeds with a high conversion when a stable radical
can form (benzhydryl and especially benzyl). It is
Reaction of alkenes with the system I II was per-
formed in benzene at 20 C. The ratio of the starting
components (alkene : alcoholate I : hydroperoxide II)
was 1 : 1 : 2. The highest conversion (up to 75%) was
observed with the most substituted alkene, 2,3-di-
methyl-2-butene, which agrees with the published
data [7].
The primary oxidation products of alkenes III VI
are tertiary allylic peroxides R2C(OOH)C(R )=CH2
[R = R = CH3 (VII); R = CH3, R = H (VIII); R =
Ph, R = CH3 (IX); R = Ph, R = H (X)]. Hydroper-
oxides VII X undergo subsequent transformations to
give unsaturated alcohols, epoxy alcohols, and car-
bonyl compounds (Table 1).
1070-3632/01/7105-0736$25.00 2001 MAIK Nauka/Interperiodica

REACTION OF TRI- AND TETRASUBSTITUTED ALKENES
737
Table 1. Products of the reaction of alkenes R2C=CR CH3 with the system (t-BuO)3Al t-BuOOH (1 : 1 : 2 molar ratio)
1
in benzene at 20 C, reaction time 24 h (mol mol of alkene)a
Reaction products
R = R = CH3
R = CH3, R = H
Volatile products
R = Ph, R = CH3
R = Ph, R = H
t-BuOH
t-BuOOH
R2C=CR CH3 (initial)
R2C=O
2.48
Traces
0.26
2.81
0.12
0.51
2.76
0.30
2.47
0.27
0.21
0.17
Me2C=O 0.12
CH3C(O)H (qualitatively)
R2C(OOH)C(R )=CH2
R2C(OH)C(R )=CH2
R2C(OH)C(R ) CH2
O
0.10
0.11
0.10
0.07
Traces
0.06
Hydrolysis products of nonvolatile residueb
t-BuOH
t-BuOOH
R2C=CR CH3 (initial)
R2C=O
R2C(OOH)C(R )=CH2
R2C(OH)C(R )=CH2
R2C(OH)C(R ) CH2
O
CH3C(O)OH
PhOH
2.20
0.25
1.82
0.23
1.59
1.98
0.26
0.35
0.30
0.11c
0.18
0.12
0.30
0.55
0.20
0.10c
0.10
0.11
0.04
0.03
0.12
0.05
CH3C(O)H (qualitatively)
0.05
0.15
0.04
0.13
0.16
0.01
0.02
0.02
0.03
PhC(O)CR =CH2
a
b
c
Averaged results. Amount of aluminum in all the experiments is 1 g-at. Hydroperoxides were identified by the products of
catalytic decomposition in the presence of benzenesulfonic acid, PhOH, and phenylalkenyl ketones.
Several pathways of formation of hydroperoxides
The possibility of this pathway was confirmed by
the reaction of alkene III with oxygen, initiated by
the system I II taken in amount of 10% relative to
alkene. Under these conditions the conversion of
alkene was 80%. All the products listed in Table 1
were isolated. The major product was hydroperoxide
VII (0.50 mol). We also performed oxidation of III
with oxygen using tert-butyl peroxalate as initiator and
obtained hydroperoxide VII and unsaturated alcohol.
can be suggested. The first is the reaction of
alkene with singlet oxygen partially generated by
the studied system [8]. The process can also be initia-
ted by tert-butoxy radicals formed by homolytic de-
composition of aluminum-containing trioxide and
identified with spin traps. tert-Butoxy radicals abstract
hydrogen from the methyl groups of alkenes III VI.
The resulting primary radical undergoes rearrange-
ment and reacts with the evolution of oxygen accord-
ing to scheme (1) [scheme (2)].
Our results do not contradict the published data on
formation of tertiary hydroperoxides in oxidation of
alkenes, because it is known that alkene III trans-
forms into hydroperoxide VII either by homolytic
oxidation in the presence of alkoxy and alkylperoxy
radicals [9] or by the reaction with singlet oxygen [10].
R
R
R
.
R
R
R
R
R
R
t-BuO
.
C C
C C
C C
.
t-BuOH
CH3
CH2
CH2
O2
R
R
R
R
H3C
H3C
CH3
CH2
.
.
O2
Alkene
RO , ROO
C C
C C
OOH
(2)
(3)
III
C C
OOH
1O2
.
R
CH2
R
CH2
OO
Along with the above-mentioned reactions, the third
pathway is possible, namely, oxidation of alkene with
available oxygen as suggested in [1, 2].
R = R = CH3 (III); R = CH3, R = H (IV); R = Ph, R =
CH3 (V); R = Ph, R = H (VI).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 71 No. 5 2001

738
MARTYNOVA et al.
At present, we cannot choose between these three
Table 2. Products of the reaction of (CH3)2C=C(CH3)2
with the system (t-BuO)3Al t-BuOOH (1 : 1 : 2) (a)
and of transformation of (CH3)2C(OOH)C(CH3)=CH2 in
the presence of (t-BuO)3Al (b) in benzene [20 C, 24 h;
pathways. More definite conclusion can be made
about further transformations of the oxidation prod-
ucts. Hydroperoxides VII X react with alcoholate I
to form new peroxy compounds of aluminum A.
1
mol mol (t-BuO)3Al]a
R
R
R
R
R
R
(t-BuO)3Al + O*2
Product
Reaction (a) Reaction (b)
C C
C C
.
.
OOH
CH3
CH2
Volatile products
2.48
R
R
t-BuOH
0.89
C C
(4)
(5)
(CH3)2C=C(CH3)2
t-BuOOH
(CH3)2C(OOH)C(CH3)=CH2
(CH3)2C=O
0.26
Traces
0.10
R
CH2
OOH
VII X
0.21
0.10
0.03
0.06
R
R
(CH3)2C(OH)C(CH3) CH2
O
VII X + (t-BuO)3Al
C C CH2 + t-BuOH
(CH3)2C(OH)C(CH3)=CH2
0.11
0.13
R
OOAl(OBu-t)2
Hydrolysis products of nonvolatile residueb
A
t-BuOH
t-BuOOH
(CH3)2C(OOH)C(CH3)=CH2
(CH3)2C=O
(CH3)2C(OH)C(CH3)=CH2
MeOH
2.20
0.25
0.03
0.04
0.12
0.04
2.03
All the other compounds listed in Table 1 are
formed by transformations of peroxides A. It was con-
firmed by the comparison of the products formed by
oxidation of 2,3-dimethyl-2-butene with the system
I II and by transformation of specially prepared hy-
droperoxide, 3-hydroperoxy-2,3-dimethyl-1-butene
VII, in the presence of aluminum tert-butylate
(Table 2).
0.16
0.13
0.20
Not de-
termined
0.06
0.20
(CH3)2C(OH)C(CH3) CH2
O
Aluminum-containing peroxides A decompose by
several pathways. One of them is the formation of
alcohols, probably by the reaction of peroxide A with
tertiary hydroperoxide similarly to the release of tert-
butanol [scheme (1)] [1 4].
a
b
Averaged results.
iments 1 g-at.
Aluminum content in all the exper-
The presence of carbonyl compounds among the
volatile products (acetone, acetaldehyde) and among
the hydrolysis products of the nonvolatile residue
(benzophenone) suggests degradation of the carbon
skeleton of alkene. In particular, Table 2 shows that
acetone is formed in the reaction of 2,3-dimethyl-2-
butene with the system I II as well as in the reaction
of the corresponding hydroperoxide with alcoholate I,
which suggests that acetone is the product of decom-
position of peroxide VII.
Epoxy alcohols are formed by intramolecular ox-
idation of the double bond [Eq. (6)]. The possibility
of epoxidation of allylic alcohols by the system I II
at 25 C was shown in [11, 12].
For example, in the case of 2,3-dimethyl-2-butene
the reaction proceeds as follows.
(6)
H3C
H3C
CH3
C C CH2
H3C
H3C
R
= t-Bu, C(CH3)2 C(CH3)=CH2.
(7)
OAl(OBu-t)2
C O + H3C C CH2
However, intermolecular epoxidation cannot be
ruled out, as it was shown for decomposition of allylic
hydroperoxides in the presence of titanium alcoholates
[13]. Direct epoxidation of the double bond by the re-
action of hydroperoxy and carbon-centered radicals
[Eq. (4)] is also possinle.
O OAl(OBu-t)2
It is known that alkenes can react with singlet oxy-
gen to form 1,2-dioxetanes decomposing to carbonyl
compounds [14]. But this reaction takes place only for
alkenes with electron-withdrawing substituents. In our
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 71 No. 5 2001

REACTION OF TRI- AND TETRASUBSTITUTED ALKENES
case formation of carbonyl compounds through de-
EXPERIMENTAL
739
composition of aluminum-containing peroxides is
more probable. The suggested scheme [Eq. (7)] is
experimentally confirmed by the reaction of 2,3-di-
methyl-2-butene with the system I II taken in an
amount of 10% relative to alkene. From the suggested
scheme (7) it follows that the amount of carbonyl
compound must coincide with the amount of alco-
holate I taken in the reaction. Indeed, in this exper-
iment only 0.1 mol of acetone was isolated, which
corresponds to the amount of aluminum tert-butylate.
The IR spectra were recorded on a Specord IR-75
spectrometer. Chromatographic analysis of the reac-
tion products in the liquid phase was carried out on
a Tsvet-2-65 chromatograph with a flame-ionization
detector and argon carrier gas. Volatile components
(tert-butanol, acetone, 2,3-dimethyl-2-butene, 2-meth-
yl-2-butene, acetaldehyde, methyl acetate) were ana-
lyzed on a 2400 3-m column, stationary phase 10%
polyethylene glycol on TZKM support, 55 70 C. For
the analysis of benzophenone, 1-phenyl-2-propen-1-
one, phenol, 1,1-diphenylpropene, 1,1-diphenyl-2-
methylpropene, 1,1-diphenyl-2-propen-1-ol, and 1,1-
diphenyl-2-methylpropen-1-ol a 3000 3-mm column
was used; stationary phase 5% SE-30 on Inerton-AW
support, 140 190 C. tert-Butyl hydroperoxide, 3-hy-
droperoxy-2,3-dimethyl-1-butene, 2,3-dimethyl-1-buten-
3-ol, 3-methyl-1-buten-3-ol, and 1-methyl-1-(1-hy-
droxy-1-methylethyl)oxirane were analyzed on an
LKhM-80 chromatograph; 1200 3-mm column, he-
lium carrier gas, stationary phase 15% dinonyl phthal-
ate on Chromaton N-AW-DMCS support, 40 80 C.
Chromatograms were processed using external ref-
erences. All the manipulations with aluminum com-
pounds were done under argon.
Hydrolysis of di-tert-butoxypropenyloxyaluminum
yields acetone. However, Table 2 shows that the
amount of acetone in the free state exceeds its amount
in the bound state, which may be due to the reaction
of excess t-BuOH with aluminum enolate [15].
(t-BuO)2AlOC(CH3) CH2
t-BuOH H+, H2O
2t-BuOH + Al(OH)3 + (CH3)2C O
(8)
(t-BuO)3Al + (CH3)2C O
Under these conditions aldehydes are oxidized to
acyloxy derivatives of aluminum. The IR spectra of
nonvolatile residues contain broad absorption bands in
1
The amount of aliphatic acids in nonvolatile re-
sidues was determined by the procedure in [16], and
the content of tert-butoxy groups was found by
the Denigés method [17]. The amount of aluminum
was determined by precipitation of aluminum hydrox-
ide and its calcination to Al2O3. Carboxylic acids
were identified in the form of methyl esters after treat-
ment with diazomethane [4]. Carbonyl compounds
were identified as 2,4-dinitrophenylhydrazones by the
melting points and by TLC on Silufol UV-254 plates,
elution with benzene. The amount of hydroperoxides
I, VII, and VIII in the volatile fraction and hydrolysis
products of the nonvolatile residue was determined
chromatographically. Quantitative analysis of hydro-
peroxides IX and X formed by oxidation of diphenyl-
substituted alkenes was performed by iodometric titra-
tion. Compounds IX and X were identified by prod-
ucts of their acid decomposition [18] (phenol and
phenyl alkenyl ketones).
the range 1570 1600 cm , characteristic of COO
stretching vibrations, and in the hydrolysis products
the carboxylic acids are found.
In the case of diphenyl-substituted alkenes the pres-
ence of phenylalkenyl ketones and phenol in the hy-
drolysis products of nonvolatile residues is due to
partial rearrangement of peroxides A and decomposi-
tion of the resulting aluminum alkoxides [Eq. (9)].
Ph
Ph
R
PhO
Ph
CH2
C C R
OAl(OBu-t)2
O
C C CH2
O OAl(OBu-t)2
PhC(O)C(R ) CH2 + PhOAl(OBu-t)2
R = H (IX), CH3 (X).
(9)
Thus, the system consisting of aluminum tris-tert-
butylate and tert-butyl hydroperoxide is a unique
oxidant of tri- and tetrasubstituted alkenes under mild
conditions. The process occurs by the radical pathway
involving the stage of formation of tertiary hydroper-
oxides and their subsequent reaction with alcoholate I
yielding new aluminum-containing peroxy compounds
A. Heterolytic decomposition of these compounds
yields the final products. The reaction occurs with
partial cleavage of the starting alkene. Oxidation of
carbon hydrogen bonds of the benzene ring was not
observed.
Aluminum tri-tert-butylate was prepared by the re-
action of tert-butanol and aluminum [19] and purified
by sublimation (160 170 C/1 mm Hg). Found, %:
Al 11.12. C12H27AlO3. Calculated, %: Al 10.96.
1,1-Diphenylpropene and 1,1-diphenyl-2-methyl-
propene were prepared by dehydration of the cor-
responding tertiary alcohols at 200 C without a sol-
vent [20]. 2,3-Dimethyl-2-butene was synthesized by
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 71 No. 5 2001

740
MARTYNOVA et al.
dehydration of 2,3-dimethyl-2-butanol with oxalic acid
[21], and 2-methyl-2-butene, by treatment of 2-meth-
yl-2-butanol with concentrated sulfuric acid [22].
and 0.35 g of Me2C(OOH)C(CH3)=CH2 in 15 ml of
benzene was kept for 24 h at room temperature and
treated as described above. The volatile fraction
contained 0.20 g of t-BuOH, 0.002 g of Me2C=O,
and 0.033 g of Me2C(OH)C(CH3)=CH2. The hy-
drolysis products contained 0.03 g of Me2C=O, 0.45 g
of t-BuOH, 0.07 g of Me2C(OOH)C(CH3)=CH2,
0.05 g of Me2C(OH)C(CH3)=CH2, 0.10 g of
2,3-Dimethyl-1-buten-3-ol [23] and 3-methyl-1-bu-
ten-3-ol [24] were prepared by treatment of methyl
acrylate or methacrylate with excess methylmagnesi-
um iodide. The refractive indices, boiling points, and
melting points of the alkenes and alcohols agree with
the published data. 1-Diphenyl-2-propen-1-ol was
prepared by treatment of methyl acrylate with phenyl-
magnesium bromide, bp 130 132 C/2 mm Hg, nD19
1.5690. Found, %: OH 8.06; bromine number 75.02.
C15H14O. Calculated, %: OH 8.10, bromine number
76.20. Phenylprop-2-en-1-one was prepared by de-
composition of the corresponding Mannich salt [25],
bp 57 59 C/2 mmHg, n1D9 1.5180, mp of 2,4-dinitro-
phenylhydrazone 264 266 C. 1-Methyl-1-(1-hydroxy-
1-methylethyl)oxirane was prepared by treatment of
2,3-dimethylbut-1-en-3-ol with tert-butyl hydroper-
oxide in the presence of vanadyl acetylacetonate [7].
Colorless liquid, bp 34 C/24 mm Hg, n1D9 1.4284. IR
, and 0.075 g of Al.
Me2C(OH)(CH3)C CH2
O
Reactions of alkenes IV VI with the system I II
and the analysis of the reaction products were per-
formed similarly. The IR spectra of nonvolatile re-
sidues after oxidation of diphenyl-substituted propenes
contain an absorption band at 1660 cm 1 characteristic
of the carbonyl stretching vibrations of benzophenone.
This fact proves that benzophenone is formed before
the hydrolysis. The melting point of authentic ben-
zophenone 2,4-dinitrophenylhydrazone and the mixed
sample is 236 C.
1
spectrum, , cm : 860, 920, 1250, 3050 (epoxy ring),
The presence of epoxy compounds in the products
was proved by the qualitative reactions such as the
coloration with pyridine on heating [27], formation of
a precipitate of silver iodate [28], and the Deckert test
[29]. Quantitative determination of epoxides was per-
formed according to [30].
3460 (OH). Found, %: OH 14.18. C6H12O2. Cal-
culated, %: OH 14.66. 3-Hydroperoxy-2,3-dimethyl-
1-butene was prepared by treatment of 2,3-dimethyl-2-
butene with 30% hydrogen peroxide and a solution of
sodium hypochlorite in anhydrous methanol [26];
bp 46 C/8 mm Hg, n1D6 1.4440. The concentration of
tert-butyl hydroperoxide was no less than 99.5 99.8%.
Hydroperoxides IX and X were identified by paper
chromatography [1], and also by formation of phenol
and phenylalkenyl ketones in the presence of p-tolu-
enesulfonic acid [4].
Reaction of 2,3-dimethyl-2-butene with the sys-
tem (t-BuO)3Al t-BuOOH in a 1 : 1 : 2 molar ratio.
A mixture of 1.70 g of (t-BuO)3Al, 1.24 g of
t-BuOOH, and 0.58 g of 2,3-dimethyl-2-butene in
20 ml of benzene was kept for 24 h at room tempera-
ture. The solution acquired an intense yellow color.
The solvent and the volatile products were distilled
into a trap cooled with liquid nitrogen. The conden-
sate contained 0.04 g of t-BuOOH, 1.16 g of
t-BuOH, 0.06 g of Me2C=O, 0.15 g of Me2C=CMe2,
0.05 g of Me2C(OOH)C(CH3)=CH2, and 0.07 g of
Me2C(OH)C(CH3)=CH2. The residue, a viscous yel-
low mass, was dissolved in diethyl ether and treated
with a 10% solution of sulfuric acid. The ether extract
contained 0.05 g of t-BuOOH, 1.15 g of t-BuOH, 0.03 g
of Me2C=O, 0.04 g of Me2C(OOH)C(CH3)=CH2,
0.11 g of Me2C(OH)C(CH3)=CH2, and 0.06 g of
The decomposition products were analyzed quali-
tatively and quantitatively.
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