Interaction of 2-Monosubstituted 1,3-Dioxolanes with Aluminacyclopentanes

Article abstract of DOI:10.1134/S0965544119060082

Abstract: The interaction of 2-monosubstituted 1,3-dioxolanes with 3-hexyl-1-ethylaluminacyclopentane leads to the cleavage of the Al–C bond of the metallocycle and the formation of ethylene glycol monoethers after hydrolysis of the resulting reaction mix

Full text of DOI:10.1134/S0965544119060082

ISSN 0965-5441, Petroleum Chemistry, 2019, Vol. 59, No. 6, pp. 650–655. © Pleiades Publishing, Ltd., 2019.
Interaction of 2-Monosubstituted 1,3-Dioxolanes
with Aluminacyclopentanes
T. F. Dekhtyar’a, *, O. S. Vostrikovab, S. S. Zlotskiib, A. A. Bogomazovaa, and N. N. Mikhailovab
aBashkir State University, Sterlitamak Branch, Sterlitamak, Bashkortostan, 453103 Russia
bUfa State Petroleum Technological University, Ufa, Bashkortostan, 450062 Russia
*e-mail: dekhtyartf@mail.ru
Received October 5, 2017; revised December 15, 2018; accepted February 12, 2019
Abstract—The interaction of 2-monosubstituted 1,3-dioxolanes with 3-hexyl-1-ethylaluminacyclopentane
leads to the cleavage of the Al–C bond of the metallocycle and the formation of ethylene glycol monoethers
after hydrolysis of the resulting reaction mixture. Catalytic amounts of ZrCl4 or Ni(acac)2 activate the pro-
cess. The reaction of 2-monosubstituted 1,3-dioxolanes with 1-ethyl-3-naphthylaluminacyclopentane yields
the product of cleavage of the exocyclic Al–Et bond of aluminacyclopentane.
Keywords: organoaluminum compounds, aluminacyclopentanes, 1,3-dioxolane, catalysis, zirconium tetra-
chloride
DOI: 10.1134/S0965544119060082
The interaction of cyclic acetals and ketals with the the required value, and the reaction mixture was
simplest organoaluminum compounds finds wide stirred for 2 or 6 h, after which it was cooled to −20°C
application in organic synthesis [1]. The use of higher and decomposed with 20 mL of 10% HCl. The organic
organoaluminum compounds (OACs), which have phase was separated, dried over MgSO4, and analyzed
become available recently, for these purposes is clearly
understudied [2, 3]. At the same time, the involve-
ment of such OACs can be very effective in relation to
the synthesis of derivatives of higher monoethers of
glycols [4] and, in addition, will make it possible to
further develop and generalize the conventional ideas
about the reaction mechanisms of 1,3-dioxolanes. In
this connection, detailed investigation of the reaction
of these carbonyl substrates with OACs of different
structures appears to be an important and relevant task
of modern organic synthesis.
Aluminacyclopentanes, five-membered alumi-
num-containing heterocycles differing from trialkylal-
anes by specific reactivity of the endocyclic Al–C
bonds, became the objects of intensive investigation in
a number of research centers after the development of
a convenient method for their synthesis on the basis of
available petrochemicals [5].
by GLC. The products were isolated by vacuum distil-
lation. Hydroxyethers (3a–3c) were identified in the
form of a mixture of regioisomers (3) and (4). Com-
pound 5b was identified in the individual form, and
monoethers 5a and 5c were identified using GLC by
matching with authentic samples [6].
Reaction of 1,3-Dioxolanes 2a–2c with 1-Ethyl-3-
Naphthylaluminacyclopentane (General Procedure)
Any of dioxolanes 2a–2c in an amount of 20 mmol
was added dropwise to a solution of 40 mmol of
1-ethyl-3-naphthylaluminacyclopentane (6) in 10 mL
of dry CH2Cl2 at 0°C in a dry argon atmosphere. The
temperature of the reaction mixture was increased to
20°C, and the mixture was stirred for 6 h, after which
it was cooled to −20°C and decomposed with 20 mL
of a 10% HCl aqueous solution. The organic phase was
separated, dried over MgSO4, and analyzed by GLC.
Product 5b was isolated by vacuum distillation; this
hydroxyether was identified in the individual form.
Monoethers 5a and 5c were identified using GLC by
matching with authentic samples [6].
EXPERIMENTAL
Reaction of 3-Hexyl-1-Ethylaluminacyclopentane
with 1,3-Dioxolanes (General Procedure)
A 20-mmol portion of dioxolane selected from
Aluminacyclopentane 1 and 1-ethyl-3-naphthylal-
compounds 2a–2c was added dropwise to a solution of uminacyclopentane 6 were synthesized according to a
40 mmol of 3-hexyl-1-ethylaluminacyclopentane (1) procedure reported in [5]. 2-Monosubstituted 1,3-
in 10 mL of anhydrous heptane at −20°C in a dry dioxolanes 2a–2c were synthesized according to a
argon atmosphere. The temperature was increased to known procedure [7], distilled over NaOH under
650

INTERACTION OF 2-MONOSUBSTITUTED 1,3-DIOXOLANES
651
argon, and stored in an inert atmosphere. Their phys- on Chromaton N-AW, a flame ionization detector,
and helium as the carrier gas.
RESULTS AND DISCUSSION
icochemical constants conformed to the published
ones [8].
1H and 13C NMR spectra were recorded in CDCl3
on a Bruker AM-300 spectrometer with operating fre-
quencies of 300.15 and 75.47 MHz, respectively, with
the 13C NMR spectra being recorded in the mode of
modulation of C–H coupling (JMODCH). The chro-
matographic analysis of the reaction mixtures was per-
formed on a Chrom-5 chromatograph using a 120 ×
We have studied the reaction of 3-hexyl-1-ethylal-
uminacyclopentane 1 with 1,3-dioxolanes 2a–2c [9],
the cleavage of which by the simplest trialkylalanes
(AlEt3 or Al-i-Bu3) leads to the formation of higher
monoethers of ethylene glycol [10]. In the case of alu-
minacyclopentanes possessing three Al–C bonds that
are nonequivalent in activity, the formation of three
0.5 cm stainless steel column packed with 5% SE-30 different monoethers 3–5 from each acetal is possible.
R2
C6H13
+
O
O
Al
R1
2a−c
1
R2
O
R2
R2
O
O
O
O
O
+
+
Al
Al
Al
R1
R1
R1
C6H13
C6H13
1) 2 h,
2) H3O+
1) 2 h,
2) H3O+
1) 6 h,
2) H3O+
R2
O
R2
R2
OH
O
OH
C6H13O
R1
4a−c
OH
R1
R1
5a−c
C6H13
3a−c
R1 = Ph, R2 = H (2−5a)
R1 = i-Ph, R2 = H (2−5b)
R1 = Ph, R2 = CH3 (2−5c)
We found that the endocyclic radicals of alumina- the yield of the aforementioned products does not
exceed 3–5%, whereas a further increase in the excess
of the organoaluminum compound does not have a
noticeable effect on the reaction course.
cyclopentane predominantly participate in the reac-
tion under study. Thus, 2-monosubstituted 1,3-diox-
olanes 2a–2c react with a double excess of aluminacy-
clopentane under mild conditions (20°C, 2 h) to form
a mixture of aluminum heterocycle opening products
3a–3c and 4a–4c in ratios depending on both the
structure of the reactant acetals and reaction condi-
Metal complex catalysts noticeable affect the regiose-
lectivity of the process, and the effect (especially of
ZrCl4) is maximum in the case of acetal 2b. Methylene
chloride, which significantly increases the yields of the
tions (Table 1). At an equimolar ratio of the reactants, products of the reactions of 1,3-dioxolanes with the sim-
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652
DEKHTYAR’ et al.
Table 1. Interaction of 2-monosubstituted 1,3-dioxolanes with 3-hexyl-1-ethylaluminacyclopentane (reaction time is 2 h
and the aluminacyclopentane : acetal ratio is 2 : 1)
Total yield
of products, %
Initial acetal
Solvent
Catalyst, 3 mol % Temperature, °C
Ratio 3/4
2a
2a
2a
2a
2a
2a
Hexane
–
ZrCl4
–
Ni(acac)2
–
ZrCl4
20
20
60
20
20
20
3a + 4a (44)
3a + 4a (71)
3a + 4a (64)
3a + 4a (77)
3a + 4a (61)
3a + 4a (75)
1.59
1.73
1.13
2.71
1.44
2.75
Hexane
Hexane
Hexane
CH2Cl2
CH2Cl2
2b
2b
2b
2b
2b
2b
Hexane
Hexane
Hexane
Hexane
CH2Cl2
CH2Cl2
–
ZrCl4
–
Ni(acac)2
–
ZrCl4
20
20
60
20
20
20
3b + 4b (52)
3b + 4b (54)
3b + 4b (65)
3b + 4b (62)
3b + 4b (54)
3b + 4b (43)
1.36
5.00
1.24
1.95
1.45
2.58
2c
2c
Hexane
Hexane
–
ZrCl4
20
20
3c + 4c (65)
3c + 4c (64)
1.03
1.00
plest OACs [11], affects the course of the reaction in an
An increase in the reaction temperature to 60°C
ambiguous manner. It increases the total yield of prod- leads to some increase in the total yield of
ucts 3a and 4a without altering regioselectivity of the hydroxyethers 3a, 3b and 4a, 4b; however, it decreases
reaction in the case of 2-phenyl-1,3-dioxolane 2a and the selectivity for compounds 3a and 3b.
increases the regioselectivity of the cleavage involving 2-
isopropyl-1,3-dioxolane 2b almost without increasing
the total yield of hydroxyethers 3b and 4b.
It is interesting to that 1 reacts with unsymmetrical
acetal 2c only at the C2–O1 bond of the dioxolane het-
erocycle to form about equal amounts of
hydroxyethers 3c and 4c, whereas monoethers with a
We showed earlier that in the case of interaction of
ethyl orthoformate with 1-ethyl-3-naphthylalumina-
cyclopentane containing a very bulky aryl substituent
at the C3 atom of the heterocycle, the endocyclic rad-
ical of aluminacyclopentane participates in the reac-
tion [12].
It appeared interesting to involve the aforemen-
secondary –OH group are not found among the prod- tioned aluminacyclopentane into the reaction with
ucts. Note that the regioselectivity of the cleavage of 1,3-dioxacyclanes. Thus, 1,3-dioxolanes 2a–2c inter-
aluminacyclopentane 1 turned out to be the lowest in act with a double excess of 1-ethyl-3-naphthylalumi-
our experiments (Table 1). In all the cases, mono- nacyclopentane 6 under mild conditions (20°C, 6 h) to
ethers 5a–5c are produced only in the case of an selectively form aluminates that yield hydroxyethers
increase in the reaction time to 6 h; however, their 5a–5c in a yield not exceeding 20% after hydrolysis of
yields do not exceed 5–10%.
the reaction mixture over 6 h.
O
HO
R2
R2 R1
+
O
O
Al
R1
2a−c
O
HO
R2 R1
6
5a−c
20%
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INTERACTION OF 2-MONOSUBSTITUTED 1,3-DIOXOLANES
653
3H, H(9II), CH3, J = 6.0 Hz), 1.15–1.45 (m, 10H,
H(4II)–H(8II), CH2), 1.45–1.55 (m, 2H, H(10II),
CH2), 1.65–1.75 (m, 2H, H(2II), CH2), 1.75–1.95 (m,
At an equimolar ratio of the reactants, the yield of
these products does not exceed 3–5%, while further
increase in the excess of the organoaluminum com-
pound has no noticeable influence on the reaction
course.
As has been found, radicals with different struc-
tures present in the composition of the same orga-
noaluminum compound differ in reactivity in this
reaction; it turned out that under the same conditions
(20°C, 2 h), aluminacyclopentane 6 did not react with
cyclic acetals by the endocyclic radical, but an increase
in the reaction time to 6 h led to the formation of the
products of cleavage of the exocyclic Al–Et bond in
the amount not exceeding 20%.
1H, H(3II), CH), 2.17 (br.s, 1H, OH), 3.43 (t, 2H,
H(2), CH2O, J = 7.7 Hz), 3.70 (t, 2H, H(1), CH2OH,
J = 7.7 Hz), 4.32 (t, 1H, H(1II), CH, J = 6.8 Hz),
7.20–7.40 (m, 5H, H(2I)–H(6I), CH, Ar). 13C NMR,
δ, ppm: 10.45 (C(11II), CH3) 13.99 (C(9II), CH3),
22.55 (C(8II), CH2), 26.03 (C(5II), CH2), 26.84
(C(10II), CH2) 29.54 (C(6II), CH2), 31.77 (C(7II),
CH2), 35.06 (C(3II), CH), 35.47 (C(4II), CH2), 42.19
(C(2II), CH2), 61.79 (C(1), CH2OH), 69.75 (C(2),
CH2O), 80.90–80.98 (C(1II), CH), 126.48–128.28
(C(2I)–C(6I), CH, Ar), 142.34 (C(1I), C, Ar).
The structure of all the obtained compounds was
determined using 1H and 13C NMR spectroscopy.
11II
2II
6II
8II
10II
11II
1II
2
O
4II
2II
6II
8II
10II
HO
1
3II
5II
7II
9II
1II
2
O
1I
4II
HO
1
3II
5II
7II
9II
6I
5I
2I
3I
1I
3I
2I
4I
2-[(1-Isopropyl-4-methyldecyl)oxy]-1-ethanol (3b).
Tb 145–150°C (40 mmHg). Found, %: C 73.36;
2-[(4-Methyl-1-phenyldecyl)oxy]-1-ethanol (3a).
Tb 120–125°C (1 mmHg). Found, %: C 78.10; H
11.00. Calcd. for C19H32O2, %: C 78.03; H 10.94. H
H 13.13. Calcd. for C16H34O2, %: C 74.36; H 13.26. 1H
NMR, δ, ppm: 0.89 (t, 3H, H(10II), CH3, J = 6.6 Hz),
0.9 (d, 3H, H(11II), CH3, J = 5.2 Hz), 0.91 (d, 6H,
H(2I), H(3I), CH3, J = 6.7 Hz), 1.05–1.55 (m, 15H,
H(2II)–H(9II) CH2, CH), 1.80–1.92 (m, 1H, H(1I),
1
NMR, δ, ppm: 0.88 (d, 3H, H(11II), CH3, J = 6.7 Hz),
0.9 (t, 3H, H(10II), CH3, J = 6.0 Hz), 1.15–1.45 (m,
11H, H(4II)–H(9II), CH2, CH), 1.65–1.75 (m, 2H,
H(3II), CH2), 1.75–1.95 (m, 2H, H(2II), CH2), 2.17
(br.s, 1H, OH), 3.43 (t, 2H, H(2), CH2O, J=7.7 Hz),
3.70 (t, 2H, H(1), CH2OH, J = 7.7 Hz), 4.20 (t, 1H,
H(1II), CH, J = 7.0 Hz), 7.20–7.40 (m, 5H, H(2I)–
H(6I), CH, Ar). 13C NMR, δ, ppm: 13.99 (C(10II),
CH3), 19.46 (C(11II), CH3), 22.55 (C(9II), CH2),
29.49 (C(7II), CH2), 29.65 (C(6II), CH2), 31.77
(C(8II), CH2), 32.58 (C(4II), CH), 32.67 (C(5II),
CH2), 35.61 (C(2II), CH2), 36.73 (C(3II), CH2), 61.79
CH), 2.25 (br.s, 1H, OH), 2.97–3.07 (m, 1H, H(1II),
CH), 3.55 (t, 2H, H(2), CH2O, J = 7.0 Hz), 3.72 (t,
2H, H(1), CH2OH, J = 7.0 Hz). 13C NMR, δ, ppm:
14.06 (C(10II), CH3), 18.03 (C(2I), CH3), 18.23
(C(3I), CH3), 19.60, 19.71 (C(11II), CH3), 22.65
(C(9II), CH2), 27.01 (C(6II), CH2), 27.72 (C(2II),
CH2), 29.63 (C(7II), CH2), 30.65 (C(4II), CH), 31.90
(C(8II), CH2), 32.76, 32.86 (C(3II), CH2), 32.90,
33.01 (C(1I), CH), 36.90 (C(5), CH2), 62.25 (C(1),
CH2OH), 70.70 (C(2), CH2O), 85.37, 85.47 (C(1II),
CH).
II
(C(1), CH2OH), 69.75 (C(2), CH2O), 83.15 (C(1 ),
CH), 126.48–128.28 (C(2I)–C(6I), CH, Ar), 142.42
(C(1I), C, Ar).
4II
4II
2II
6II
8II
2II
6II
8II
1II
3II
1II
3II
O
2
2
O
HO
1
HO
1
5II
11II
7II
9II
5II
11II
7II
9II
10II
10II
1I
1I
3I
2I
6I
5I
2I
3I
2-[(1-Isopropylnonyl-3-ethyl)oxy]-1-ethanol (4b).
Tb 145–150°C (40 mmHg). Found, %: C 73.36; H
4I
1
13.13.Calcd. for C16H34O2, %: C 74.36; H 13.26. H
2-[(1-Phenylnonyl-3-ethyl)oxy]-1-ethanol (4a). Tb
120–125°C (1 mmHg). Found, %: C 78.10; H 11.00.
NMR, δ, ppm: 0.87 (t, 3H, H(11II), CH3, J = 6.7 Hz),
Calcd. for C19H32O2, %: C 78.03; H 10.94. 1H NMR, 0.91 (d, 6H, H(2I), H(3I), CH3, J = 6.7 Hz), 0.92 (t,
δ, ppm: 0.84 (t, 3H, H(11II), CH3, J = 5.1 Hz), 0.86 (t, 3H, H(9II), CH3, J = 6.9 Hz), 1.05–1.55 (m, 15H,
PETROLEUM CHEMISTRY Vol. 59 No. 6 2019

654
DEKHTYAR’ et al.
H(2II)–H(8II), H(10II), CH2, CH), 1.80–1.92 (m, 1H, CH2), 36.04 (C(2II), CH2), 36.80 (C(3II), CH2), 65.65
H(1I), CH), 2.25 (br.s, 1H, OH), 3.13–3.21 (m, 1H, (C(1), CH2OH), 74.27 (C(2), CH2O), 81.71 (C(1II),
H(1II), CH), 3.55 (t, 2H, H(2), CH2O, J = 7.0 Hz),
CH), 126.60–128.49 (C(2I)–C(6I), CH, Ar), 143.98
3.72 (t, 2H, H(1), CH2OH, J = 7.0 Hz). 13C NMR, δ, (C(1I), C, Ar).
ppm: 10.30, 10.78 (C(11II), CH3), 14.06 (C(9II), CH3),
17.66, 17.83 (C(3I), CH3), 18.13, 18.20 (C(2I), CH3),
4II
1
2II
6II
8II
1II
3II
10II
2
3
O
23.02 (C(8II) CH2), 26.23 (C(5II), CH2), 27.01
HO
5II
11II
7II
9II
1I
(C(10II), CH2), 29.63 (C(6II), CH2), 30.61, 30.65
(C(3II) CH), 31.90 (C(7II), CH2), 33.72, 34.30 (C(4II),
CH2), 35.59 (C(1I), CH), 37.08 (C(2II), CH2), 62.25
(C(1), CH2OH), 70.47 (C(2), CH2O), 82.80 (C(1II),
CH2).
6I
5I
2I
3I
4I
2-[(1-Phenylnonyl-3-ethyl)oxy]-1-propanol (4c).
Tb 180–185°C (5 mmHg). Found, %: C 78.40; H
2II
1II
1I
1
O
12.01. Calcd. for C20H34O2, %: C 78.38; H 11.18. H
1
HO
3II
2
NMR, δ, ppm: 0.85 (t, 3H, H(11II), CH3, J = 7.1 Hz),
0.95 (t, 3H, H(9II), CH3, J = 6.6 Hz), 1.13 (d, 3H,
H(3), CH3, J = 5.8 Hz), 1.15–1.95 (m, 15H, H(2II)–
H(8II), H(10II)CH2, CH), 2.11 (br.s, 1H, OH), 3.49 (t,
2H, H(1), CH2OH, J = 6.6 Hz), 3.50–3.60 (m, 1H,
H(2), CH2O), 7.20–7.40 (m, 5H, H(2I)–H(6I), CH,
Ar). 13C NMR, δ, ppm: 10.53 (C(11II), CH3), 14.06
(C(9II), CH3), 17.64 (C(3), CH3), 22.64 (C(8II),
CH2), 26.05, 26.37 (C(10II), CH2), 26.11 (C(5II),
CH2), 29.66 (C(6II), CH2), 31.86 (C(7II), CH2), 35.21
(C(3II), CH), 35.91 (C(4II), CH2), 42.71, 42.77
(C(2II), CH2), 65.75 (C(1), CH2OH), 74.45 (C(2),
CH2O), 79.49 (C(1II), CH), 126.60–128.49 (C(2I)–
C(6I), CH, Ar), 143.90 (C(1I), C, Ar).
3I
2I
2-(2-Methyl-1-ethylpropoxy)-1-ethanol (5b). Tb
72°C (10 mmHg). nD20 1.4357. Found, %: C, 65.70; H,
1
12.20. Calcd. for C8H18O2, %: C, 65.71; H, 12.41. H
NMR, δ, ppm: 0.73 (d, 3H, CH3, J = 6.8 Hz), 0.77 (d,
3H, CH3, J = 6.9 Hz), 0.8 (t, 3H, CH3, J = 7.1 Hz),
1.25–1.42 (m, 2H, CH2), 1.7 (octet, 1H, CH, J =
6.6 Hz), 2.83 (q, 1H, CHO, J = 6.5 Hz), 3.0 (br.s, 1H,
OH), 3.42 (t, 2H, CH2O, J = 4.6 Hz), 3.56 (t, 2H,
CH2O, J = 4.6 Hz). 13C NMR, δ, ppm: 9.68 (CH3),
18.0 (CH3), 18.09 (CH3), 22.85 (CH2), 30.22 (CH),
61.82 (CH2OH), 70.86 (CH2O), 86.24 (CHO).
11II
The twinning of some signals of carbon atoms due
to the formation of diastereomeric products
was observed in the spectra of compounds 3a–3c and
4a–4c.
2II
6II
8II
10II
4II
1II
2
O
HO
1
3II
5II
7II
9II
1I
6I
5I
2I
3I
In summary, the reaction of 1,3-dioxolanes with 3-
hexyl-1-ethylaluminacyclopentane can serve as a con-
venient method for the synthesis of 2-hydroxyethyl
ethers of branched secondary and tertiary higher alco-
hols that are hardly obtainable using other preparation
methods. The influence of activating additives on the
regioselectivity of the reaction and the yield of the
desired products is ambiguous and depends on the
nature and position of the substituents in the reactant
acetals.
4I
2-[(4-Methyl-1-phenyldecyl)oxy]-1-propanol (3c).
Tb 180–185°C (5 mmHg). Found, %: C 78.40; H
1
12.01. Calcd. for C20H34O2, %: C 78.38; H 11.18. H
NMR, δ, ppm: 0.85 (t, 3H, H(10II), CH3, J = 7.0 Hz),
0.90 (d, 3H, H(11II), CH3, J = 5.7 Hz), 1.13 (d, 3H,
H(3), CH3, J = 5.8 Hz), 1.15–1.95 (m, 15H, H(2II)–
H(9II), CH2, CH), 2.11 (br.s, 1H, OH), 3.45 (t, 2H,
H(1), CH2OH, J = 5.2 Hz), 3.50–3.60 (m, 1H, H(2),
CH2O), 7.20–7.40 (m, 5H, H(2I)–H(6I), CH, Ar).
13C NMR, δ, ppm: 14.06 (C(10II), CH3) 17.56 (C(3),
CH3), 19.55 (C(11II), CH3), 22.64 (C(9II), CH2),
29.57 (C(7II), CH2), 29.71 (C(6II), CH2), 31.86
(C(8II), CH2), 32.75 (C(4II), CH), 35.91 (C(5II),
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Translated by E. Boltukhina
PETROLEUM CHEMISTRY Vol. 59 No. 6 2019