(3-Hydroxy-3-methylbutyn-1-yl)cycloalkan-1-ols in the ritter reaction

Article abstract of DOI:10.1023/B:RUGC.0000042602.58177.2a

(3-Hydroxy-3-methylbutyn-1-yl)cycloalkan-1-ols were prepared by the action of (2-lithiooxy-2-methylbutyn-3-yl)lithium on cyclopentanone, cyclohexanone, cycloheptanone, and cyclododecanone. The products react with acetonitrile under Ritter reaction conditions. Therewith, in the presence of 8 g-equiv of sulfuric acid, a 2:1 mixture of 1-acetylamino-1-(2-acetylamino-2-methylbutyn-3-yl) cycloalkanes and 1-acetylamino-1-(3-acetylamino-3-methylbutyryl)cycloalkanes is formed, whereas in the presence of 2 g-equiv of the acid, a mixture of 1-acetylamino-1-(2-acetylamino-2-methylbutyn-3-yl)cycloalkanes and 1-acetylamino-1-(3-methyl-2-butenoyl)cycloalkanes in the same ratio.

Full text of DOI:10.1023/B:RUGC.0000042602.58177.2a

Russian Journal of General Chemistry, Vol. 74, No. 6, 2004, pp. 897 902. Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 6, 2004,
pp. 972 977.
Original Russian Text Copyright
2004 by Koval’skaya, Kozlov, Dikusar.
(3-Hydroxy-3-methylbutyn-1-yl)cycloalkan-1-ols
in the Ritter Reaction
S. S. Koval’skaya, N. G. Kozlov, and E. A. Dikusar
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk, Belarus
Received June 7, 2002
Abstract (3-Hydroxy-3-methylbutyn-1-yl)cycloalkan-1-ols were prepared by the action of (2-lithiooxy-2-
methylbutyn-3-yl)lithium on cyclopentanone, cyclohexanone, cycloheptanone, and cyclododecanone. The
products react with acetonitrile under Ritter reaction conditions. Therewith, in the presence of 8 g-equiv of
sulfuric acid, a 2:1 mixture of 1-acetylamino-1-(2-acetylamino-2-methylbutyn-3-yl)cycloalkanes and 1-acetyl-
amino-1-(3-acetylamino-3-methylbutyryl)cycloalkanes is formed, whereas in the presence of 2 g-equiv of the
acid, a mixture of 1-acetylamino-1-(2-acetylamino-2-methylbutyn-3-yl)cycloalkanes and 1-acetylamino-1-
(3-methyl-2-butenoyl)cycloalkanes in the same ratio.
1
Acetylenic alcohols are widely used in organic
synthesis owing to their high reactivity [1 4]. We
previously studied transformations of certain ethynyl-
carbinols under Ritter reaction conditions [5, 6] and
found that the reactivity of their triple bond varies
over a wide range.
bands characteristics of amide carbonyl ( 1660 cm )
1
and NH ( 3380 and 1540 cm ) groups, as well as a
very weak band at 2240 cm assignable to the triple
bond, the major reaction products are 1-acetylamino-
1-(3-acetylamino-3-methylbutyn-1-yl)cycloalkanes
IVa IVd formed by substitution of hydroxy groups
in the starting diols by amide, not involving the triple
1
In the present work we dwelt on transformations
under Ritter reaction conditions of acetylenic diols,
such as (2-hydroxy-2-methylbutyn-3-yl)cyclopentan-,
-cyclohexan-, -cycloheptan-, and -cyclododecan-1-ols.
It was expected that these compounds would undergo
transformations similar to those we observed earlier,
since their hydroxy groups each are attached to
1
bond (see scheme). The H NMR spectra, too, provide
evidence for the proposed structures. The spectra
contain singlet signals of terminal methyl groups, that
appear upfield from the respective signals of the start-
ing diols (by 1.35 ppm), as well as signals of amide
acetyl (two singlets near 1.9 ppm) and two NH groups
(Table 2).
tertiary carbon located
to the triple bond. Con-
The IR spectra of the minor components of the
reaction mixtures, too, contain amide vibration bands
(Table 1) but lack the C C band at 2240 cm and
sequently, the resulting carbocations can be
stabilized by conjugation with the -electron system
of the triple bond. As we showed in [5], this favors a
much faster hydration of the triple bond, under milder
conditions, in the absence of mercury catalysts.
1
1
contain a band at 1720 cm , characteristic of ketone
carbonyl. Obviously, the minor components are
amides with hydrated triple bond, and, therewith, only
one of the two possible diamidoketones is present
Starting diols IIIa IIId were prepared by a
standard procedure [7] by the action of (3-lithiooxy-
3-methylbutyn-1-yl)lithium (I) on cycloalkanones
IIa IId (see scheme and Experimental). The structure
of cycloalkanelbutynediols IIIa IIId was proved by
1H and IR spectroscopy (Tables 1 and 2).
1
(GLC data). The H NMR spectra of the isolated di-
amides show, along with methyl and acetylamino
signals (Table 2), two-proton singlets at 3.1 ppm,
characteristic of methylene groups adjacent to car-
bonyl and amido groups. These spectral data comply
with both the possible hydration products, 1-acetyl-
amino-1-(3-acetylamino-3-methylbutyryl)cycloal-
kanes V and 1-acetylamino-1-(3-acetylamino-1-oxo-
3-methylbutyl)cycloalkanes VI. Structure V may be
preferred, since the signals of terminal methyl groups
are rather upfield ( 1.30 ppm), whereas if these
groups were adjacent to the carbonyl group, as in
compound IV, the corresponding signals would have
It was found that the products of the Ritter reaction
in the presence of excess sulfuric acid (8 g-equiv),
after removal of polymeric admixtures, were two-
component mixtures (ratio 2:1). The mixtures were
separated by crystallization from ether ethanol and
ether methanol mixtures. Structural assessment of the
major components of the mixtures creates no prob-
lems. Since the IR spectra of these compounds contain
1070-3632/04/7406-0897 2004 MAIK Nauka/Interperiodica

898
KOVAL’SKAYA et al.
NHCOCH3
O
(CH2)n
(CH2)n
O
(CH2)n
(CH2)n
NHCOCH3
O
O
CH3CONH
IIa IId
XVIII
VIII
VI
I
OH
OH
OH
H+
H+
(CH2)n
Polymer
(CH2)n
(CH2)n
OH
IIIa IIId
X
XIX
H+
CH3CN
NHCOCH3
OH
NHCOCH3
CH3CONH
N
1) CH3CN
2) H2O
(CH2)n
(CH2)n
(CH2)n
(CH2)n
OH
IX
XVI
XVII
IVa IVd
1) CH3CN
2) H2O
CH3CN
OH
OH
(CH2)n
(CH2)n
(CH2)n
N
NHCOCH3
XIII
XI
XVII
NHCOCH3
NHCOCH3
1) CH3CN;
2) H2O
NHCOCH3
1) CH3CN;
2) H2O
H+
(CH2)n
(CH2)n
(CH2)n
(CH2)n
O
O
O
OH
XV
CH3CONH
XIV
VIIa VIId
n = 0 (a), 1 (b), 2 (c), 7 (d).
Va Vd
1
been shifted downfield. Conclusive evidence for the
structure of the isolated diamidoketones was obtained
chemically. It was found that the Ritter reaction of
diols IIIa IIId in the presence of 2 g-equiv of sul-
furic acid, too, gives a mixture of two amines in a
2:1 ratio, and the major components of the reaction
mixtures are identical to diamides IV and have a triple
bond in the side chain. The minor components of the
reaction mixtures were identified, on the basis of H
and IR data, as 1-acetylamino-1-(3-methyl-2-butenoyl)-
cycloalkanes VIIa VIId. The IR spectra of com-
1
pounds VII contain bands at 3375 and 1525 cm ,
characteristic of amide NH groups, as well as an
amide carbonyl absorption band at 1660 cm . The
band at 1680 cm relates to absorption of the car-
1
1
bonyl group in , -unsaturated ketones and the band
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(3-HYDROXY-3-METHYLBUTYN-1-YL)CYCLOALKAN-1-OLS IN THE RITTER REACTION
899
Table 1. Yields, melting points, and IR spectra of compounds III V and VII
Comp. Yield,
mp,
C
1
IR spectrum, cm
no.
%
IIIa
53
69
85
82
32
34
35
38
14
57 59 3275 (OH), 2980, 2940, 2870 (CH), 2240 (C C)
102 104 3350 (OH), 2980, 2855 (CH), 2230 (C C)
122 123 3340 (OH), 2975, 2930, 2855 (CH), 2230 (C C)
110 112 3320 (OH), 2935, 2855, 2845 (CH), 2230 (C C)
85 87 3380, 3070 (NH), 2955, 2870 (CH), 2240 v.s (C C), 1655 v.s (2C=O amide), 1540 (NH)
164 167 3350, 3080 (NH), 2935, 2855 (CH), 2240 v.s (C C), 1655 v.s (2C=O amide), 1540 (NH)
134 135 3385, 3070 (NH), 2925, 2855 (CH), 2240 v.s (C C), 1660 v.s (2C=O amide), 1540 (NH)
192 194 3400, 3080 (NH), 2930, 2855 (CH), 2240 v.s (C C), 1660 v.s (2C=O amide), 1540 (NH)
128 130 3380, 3080 (NH), 2955, 2940, 2870 (CH), 1720 s (C=O, ketone), 1660 v.s (2C=O amide),
1540 (NH)
IIIb
IIIc
IIId
IVaa
IVb
IVc
IVd
Va
Vb
16
17
18
16
164 165 3360, 3080 (NH), 2940, 2920, 2855 (CH), 1720 s (C=O, ketone), 1660 v.s (2C=O amide),
1540 (NH)
146 148 3390, 3080 (NH), 2945, 2925, 2910, 2855 (CH), 1720 s (C=O, ketone), 1660 v.s (2C=O amide),
1540 (NH)
170 172 3400, 3080 (NH), 2930, 2900, 2855 (CH), 1720 s (C=O, ketone), 1660 v.s (2C=O amide),
1540 (NH)
151 152 3370 (NH), 2960, 2940, 2870, 2850 (CH), 1680 s (conjud. ketone C=O), 1660 v.s (C=O amidn.),
1620 s
Vc
Vd
VIIa
(conjud. C=C), 1530 (NH)
VIIb
VIIc
VIId
17
18
20
212 213 3360 (NH), 2960, 2940, 2870, 2850 (CH), 1680 s (conjud. ketone C=O), 1660 v.s (C=O amidn.),
1620 s (conjud.
C=C), 1530 (NH)
197 198 3380 (NH), 2960, 2945, 2920, 2870, 2850 (CH), 1680 s (conjud. ketone C=O), 1660 v.s
(amide C=O), 1620 s (conjud. C=C), 1525 (NH)
224 225 3375 (NH), 2960, 2950, 2930, 2900, 2860, 2850 (CH), 1680 s (conjud. ketone C=O), 1660 v.s
(amide C=O), 1620 s (conjud. C=C), 1525 (NH)
a
The yields of diamides IVa IVd in reactions with 2 g-equiv of sulfuric acid; the yields in reactions with 8 g-equiv of sulfuric acid
are lower by 2 4% because of the slightly stronger polymer formation.
Table 2. 1H NMR spectra of compounds III V and VII, , ppm
Comp.
no.
CH2, side-chain
CH
Terminal CH3
H ring
NH, OH
COCH3
IIIa
IIIb
IIIc
IIId
IVa
1.53 s
1.54 s
1.52 s
1.51 s
1.35 s
1.51 2.20
m
m
m
m
(8H)
(10H)
(12H)
(22H)
2.59
3.08
3.00
br.s
br.s
br.s
1.20 1.80
1.40 2.20
1.20 1.95
2.25 br.s, 2.45 br.s
2.10 2.30 m (4H), 1.55 1.85m 5.50 br.s, 5.70 br.s 1.86 s, 1.96 s
(4H)
IVb
IVc
IVd
Va
1.35 s
1.34 s
1.32 s
1.28 s
2.05 2.20 m (4H), 1.30 1.80 m 5.56 br.s, 5.80 br.s 1.84 s, 1.99 s
(6H)
2.10 2.25 m (4H), 1.45 1.80 m 5.55 br.s, 5.85 br.s 1.83 s, 1.98 s
(8H)
2.05 2.25 m (4H), 1.30 1.80 m 5.56 br.s, 5.90 br.s 1.85 s, 1.97 s
(18H)
2.15 2.40 m (4H), 1.50 1.80 m 5.50 br.s, 6.10 br.s 1.92 s, 1.97 s
(4H)
3.10 s
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 6 2004

900
KOVAL’SKAYA et al.
Table 2. (Contd.)
Comp.
no.
CH2, side-chain
Terminal CH3
ring H
NH, OH
COCH3
CH
Vb
1.28 s
1.27 s
1.26 s
3.08 s
3.06 s
3.05 s
2.15 2.30 m (4H), 1.30 1.75 m 5.60 br.s, 6.16 br.s 1.90 s, 2.00 s
(6H)
2.15 2.35 m (4H), 1.40 1.80 m 5.56 br.s, 6.15 br.s 1.90 s, 2.00 s
(8H)
2.10 2.35 m (4H), 1.30 1.80 m 5.60 br.s, 6.12 br.s 1.92 s, 1.99 s
(18H)
Vc
Vd
VIIa
VIIb
VIIc
VIId
2.14 d, 1.88 d (J 1.4 Hz) 6.35 d (J 1.4 Hz) 1.70 1.90 m (4H), 1.30 1.50 m 5.60 br.s
1.99 s
1.98 s
1.97 s
1.95 s
(4H)
2.14 d, 1.88 d (J 1.4 Hz) 6.33 d (J 1.4 Hz) 1.65 1.85 m (4H), 1.25 1.45 m 5.55 br.s
(6H)
2.13 d, 1.87 d (J 1.4 Hz) 6.31 d (J 1.4 Hz) 1.65 1.80 m (4H), 1.25 1.50 m 5.55 br.s
(8H)
2.12 d, 1.87 d (J 1.4 Hz) 6.29 d (J 1.4 Hz) 1.60 1.80 m (4H), 1.20 1.40 m 5.45 br.s
(18H)
1
at 1620 cm , to absorption of its conjugated double
chain contains a triple bond and, therefore, is this
strictly linear, the iminium cationic center cannot
approach the , -hydroxy group, because this requires
a substantial distortion of bond angles. As a result,
the iminium cation reacts with a foreign hydroxy
group, giving rise to polymer formation. Evidence for
this reasoning comes from the observation in the IR
spectrum of the isolated polymeric product (see
1
bond. The H NMR spectra of the resulting com-
pounds show a multiplet (7 lines; J 1.4 Hz) at
6.30 ppm, assignable to the olefin proton in the , -
unsaturated fragment, as well as two doublets at 1.85
and 2.1 ppm, assignable to the methyl groups at the
conjugated double bond. The coupling constant of
1.4 Hz relates to allyl coupling between methyl
protons and the proton at the side-chain C2 atom.
Signals of one acetylamino group are also observed
1
Experimental) of a broad band near 1660 cm ,
characteristic of N=C O vibrations. The fraction of
this polymer gets smaller if more solvent is used to
perform the reaction (16 20-fold excess of acetonitrile
with respect to substrate). The other, smaller fraction
of the polymer, whose IR spectrum contains no such
band, results, as will be shown below, from polyme-
rization of (2-hydroxy-2-methylbutyn-3-yl)cycloal-
kenes formed by dehydration of the starting diols.
1
(Table 2). The above set of signals in the H NMR
spectrum corresponds to structure VII, since in the
case of the alternative amidoketone VIII, the signals
of terminal methyl groups would appear in a much
stronger field, whereas downfield signals would
belong to two ring methylene groups located to the
semicyclic double bond.
Obviously, amidoketones VIIa VIId obtained in
relatively mild conditions convert into diamidoketones
V in more severe conditions, and it is the latter struc-
ture that should be assigned to the above compounds.
The formation of such products suggests that water
has added by a sterically stronger shielded carbon
atom of the triple bond and, consequently, that the
reaction is thermodynamically controlled.
Since the fraction of nonhydrated compounds IV
in the reaction mixture is independent of the amount
of sulfuric acid, we can suggest that the triple bond in
amides IV undergoes no direct hydration; otherwise,
the fraction of compounds V obtained in more severe
conditions would be smaller. These suggestions allow
us to propose the above scheme.
It should be noted that the reaction is accompanied
by strong polymer formation. This can be explained
by the presence of two hydroxy groups in the mole-
cule. It is known [8] that many diols under Ritter re-
action conditions give heterocyclic derivatives
(oxazoles, oxazines, etc.) via intramolecular reaction
of the hydroxy group and the iminium carbocation
formed by nitrile addition. Since in our case the side
Since the hydroxy groups in diols III have similar
environments, protonation and subsequent elimination
of each of them to give cations IX or X, respectively,
should occur at comparable rates. Cation IX with the
positive charge in the side chain can transform along
two different pathways. In the first case, it takes up a
nucleophile molecule to form intermediate XI which
transforms into cation XII via migration of the hydr-
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(3-HYDROXY-3-METHYLBUTYN-1-YL)CYCLOALKAN-1-OLS IN THE RITTER REACTION
901
1
oxy group to the iminium cationic center. The latter
takes up a further acetonitrile molecule and is hyd-
rated to give the major reaction product, unsaturated
diamide IV. In the second case, conjugation of the
cationic center of intermediate IX with the triple bond
induces the positive charge on C4. The migration of
the hydroxy group to this atom, like that observed in
the Meyer Schuster rearrangement [3], provides
enone cation XIV. Addition to latter of an acetonitrile
molecule followed by hydration gives rise to amido-
ketone VII that, in mild reaction conditions, is the
final reaction product. In the presence of excess
sulfuric acid, the enone fragment undergoes protona-
tion to form intermediate XV whose transformations
lead to diamidoketone V.
1660 cm ) [9]. The proposed steric structure is con-
1
sistent with the H NMR spectra of compounds VIIa
VIId: The signal of one of the methyl groups appears
strongly downfield, implying proximilty of this group
to carbonyl. Such configuration of amidoketones VIIa
VIId is explained by steric factors. As seen from the
proposed scheme, has the S-trans configuration been
realized, the van der Waals radii of terminal methyl
and ring , -methyl groups would have overlapped.
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
Cation X formed by elimination of the other
hydroxy group, too, can transform into diamide IV
via intermediates XVI and XVII that are similar to
ions XI and XII. It might be expected that the rear-
rangement of cation X, similar to that described
above, would give enone ion XVIII with a semicyclic
double bond, and further amidoketones VIII and VI.
However, as mentioned above, no expected com-
pounds formed under the reaction conditions.
H
H
N
H
H
N
Ac
S-trans-V
Ac
S-cis-V
Thus, owing the possibility of conjugation between
the cationic center and the triple band, the Ritter reac-
tion of diols IIIa IIId involves, along with the simple
substitution of the hydroxy groups by amide, hydra-
tion of the triple bond. The latter process is made
possible by the isomerization of the -hydroxypro-
paryl carbocation into -enone. Obviously, the ratio
of nonhydrated products IV and hydrated products V
or VII is determined by the relative rates of nucleo-
philic addition and isomerization, which explains
why this ratio only slightly depends on the amount
of acid.
The explanations for this seemingly strange result
can be found in the properties of diols III. When
synthesized these compounds we found that they are
extremely susceptible to dehydration into conjugated
enynes XIX. Thus, in particular, on attempted vacuum
distillation at 80 C cyclopentane diol IIIa de-
hydrated by more than 50%. Probably, under our re-
action conditions, the stabilization of cyclic carboca-
tion X by proton expulsion and formation of enyne
XIX proves thermodynamically more favorable than
its isomerization into ion XVIII, which explains the
lack among the reaction products of amides VI or
VIII. At the same time, enyne XIX which is che-
mically equivalent to diol III as a substrate of the
Ritter reaction partially transforms into diamide IV as
a result of the reversibility of protonation deprotona-
tion and partially, most likely, polymerizes to form
the less polar fraction of the polymeric products.
The IR spectrum of these polymeric products lacks
EXPERIMENTAL
The IR spectra were measured on a Nicolet Protege-
460 Fourier spectrometer. The H NMR spectra were
obtained on a Tesla BS-567 spectrometer (100 MHz),
solvent CDCl3, internal reference HMDS. The reac-
tion progress and product purity were controlled by
1
GLC
on
Chrom-5,
stainless-steel
column
(2000 2 mm), packing Apiezon L on Chromaton
N-AW-DMCS (0.16 0.20).
1
the band at 1660 cm , implying that they do not
result from intermolecular reaction of iminium inter-
mediates with alcohols.
(3-Hydroxy-3-methylbutyn-1-yl)cycloalkan-1-ols
(general procedure). A solution of 70 mmol of BuLi
in hexane was slowly added with vigorous stirring
under argon to a solution of 35 mmol of anhydrous
2-methylbut-3-yn-2-ol in 100 of THF cooled to 30 C.
After 1-h stirring, 25 mmol of ketone was added, and
stirring was continued for an additional 3 h. The
temperature of the reaction mixture was gradually
raised to ambient, after which the reaction mixture
It should be noted that the enone fragment in
amidoketones VIIa VIId has an S-cis configuration,
as evidenced by the roughly equal intensities of the
C=O and C=C absorption bands ( 1680 and
1
1620 cm ) in their IR spectra and the relatively low
intensity of the first of these bands (much lower than
the intensity of the amide carbonyl band at
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 6 2004

902
KOVAL’SKAYA et al.
was left to stand overnight. The alcoholates that
formed were decomposed with caution with water and
then 300 ml of water was added. The mixture was
treated with ether. The extracts were washed with
water and dried with CaCl2. The solvent was removed,
and the products were purified by recrystallization
from hexane.
and VIIa were obtained by reprecipitation with ether.
The mother liquors that contained butynyldiamides
with admixtures V or VII were evaporated to dryness,
dissolved in a minimum of absolute ethanol, the ad-
mixtures were separated by repeated treatment with
ether, and the residues were evaporated and subjected
to a vacuum. Thus obtained diamide Va was a thick
oil that gradually crystallized on standing. The other
diamides drop as white crystals. If required, they were
further purified by recrystallization from ethanol.
Ritter reaction. Concentrated sulfuric acid, 1.2 or
4.6 ml, was slowly added with cooling (5 10 C) to a
solution of 10 mmol of diol in 20 ml of acetone. The
temperature of the reaction mixture was gradually
(over the course of 3 4 h) raised to ambient, and stir-
ring was continued until the reaction was complete
(control by GLC). The reaction mixture was then
poured with caution to excess aqueous ammonia,
treated with ether (a greater volume of the extractant
was used, since amidoketones V and VII are sparingly
soluble in ether), and the extracts were dried with
MgSO4. The solvent was removed to leave a mixture
that contained up to 50% of polymers. Hexane was
added to the residue to dissolve most low-polar
polymer (polymerized enynes XIX). The solution was
decanted, and the residue was dissolved in ethanol.
Undissolved part (polymer formed by an intermole-
cular Tielmans reaction) was filtered off. The filtrate
was passed through a bed of silica gel (Chemapol
L 40/100) to remove residual polymer. The resulting
alcoholic solution that contained a mixture of diamide
IV and diamidoketone V, or diamide IV and amido-
ketone VII in a 2:1 ratio was concentrated in a
vacuum to 5 6 ml and then diluted with ether with
causion. Products V and VII that are poorly soluble
in ether precipitated. Therewith, amidoketones Vb
Vd and VIIb VIId were isolated as individual crys-
talline substances. Compounds Va and VIIa were
isolated as thick oily substances with a considerable
admixture of diamide IVa. This oil was dissolved in a
minimum of dry methanol, and pure compounds Va
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