Electrophile-initiated lactonization of 7-phenytricyclo[4.1.0.0 2,7]heptane-1-carboxylic acid

Article abstract of DOI:10.1023/B:RUJO.0000019732.37554.24

Treatment of 7-phenyltricyclo[4.1.0.0^2,7]heptane-1-carboxylic acid with benzenesulfenyl chloride, mercury acetate, and hydrogen chloride leads to cleavage of the central C-C bond in the bicyclobutane fragment and heterocyclization to substitute

Full text of DOI:10.1023/B:RUJO.0000019732.37554.24

Russian Journal of Organic Chemistry, Vol. 39, No. 12, 2003, pp. 1710 1715. Translated from Zhurnal Organicheskoi Khimii, Vol. 39, No. 12, 2003,
pp. 1782 1787.
Original Russian Text Copyright
2003 by Razin, Zolotarev.
Electrophile-Initiated Lactonization
of 7-Phenytricyclo[4.1.0.02,7]heptane-1-carboxylic Acid
V. V. Razin and R. N. Zolotarev
St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198904 Russia
Received April 4, 2003
Abstract Treatment of 7-phenyltricyclo[4.1.0.02,7]heptane-1-carboxylic acid with benzenesulfenyl chloride,
mercury acetate, and hydrogen chloride leads to cleavage of the central C C bond in the bicyclobutane
fragment and heterocyclization to substituted bicyclo[3.1.1]heptane-6,7-carbolactones.
We previously found [1, 2] that 1-phenyltricyclo-
as benzenesulfenyl chloride, mercury acetate, hydro-
gen chloride, bis(benzonitrile)dichloropalladium(II),
and iodotrimethylsilane (generated in situ). It should
be noted that all these reagents were shown to be
suitable for lactonization of unsaturated carboxylic
acids [4]. The reaction of benzenesulfenyl chloride
with acid III in methylene chloride in the presence
of triethylamine gave the expected product, phenyl-
sulfanyl-substituted lactone IVd in a high yield
(Scheme 2). Treatment of acid III with mercury
acetate in CH2Cl2 leads to heterocylization with
formation of lactone IVe (X = OAc). The latter was
converted via exchange reaction into the correspond-
ing bromomercurio and chloromercurio derivatives
IVe (X = Br, Cl). The reaction of IVe (X = Br) with
bromine gave known bromo lactone IVa, and com-
pound IVe (X = Cl) was treated with a solution of
hydrogen chloride in CH2Cl2 to obtain lactone IVf.
The same product (IVf) was also synthesized by
reduction of IVa with tributylstannane.* We made
an attempt to obtain lactone IVf directly from acid
III. We succeeded in effecting this transformation by
the action of hydrogen chloride in methylene chloride,
the yield of IVf being nearly quantitative. Lactone
IVf was also synthesized in a considerably lower yield
by prolonged heating of acid III in boiling acetonitrile
in the presence of PdCl2(PhCN)2. Taking into account
the data of [6], lactonization of acid III is initiated
by hydrogen chloride which is formed by reaction of
palladium chloride with traces of moisture.
[4.1.0.02,7]heptane (I) takes up various nucleophiles
NuH in the presence of electrophiles. Here, the addi-
tion of electrophile E+ occurred predominantly (or
exclusively) at the C1 C7 bond with strict endo-
stereoselectivity and regioselectivity (at the -position
with respect to the phenyl group), yielding norpinane
derivatives II. 7-Phenyltricyclo[4.1.0.02,7]heptane-1-
carboxylic acid III is a functionally substituted
derivative of I, which has a carboxy group at the
C1 C7 bond. Taking into account the orienting
effect of the phenyl group, we anticipated that acid
III should undergo lactonization by the action of
electrophiles. In fact, the first example of such trans-
formation is the reaction of acid III with N-halo-
succinimides (NHS) to afford halogen-substituted
lactones IVa IVc [3] (Scheme 1).
In the present work we studied transformations of
acid III, initiated by other electrophilic reagents, such
Scheme 1.
Obviously, the formation of lactones IVd, IVe
(X = OAc), and IVf, as well as of halogen-substituted
lactones IVa IVc prepared previously, involves
____________
*
I, X = H; III, X = CO2; IV, Hlg = Br (a), Cl (b), I (c).
For preliminary communication, see [5].
1070-4280/03/3912-1710$25.00 2003 MAIK Nauka/Interperiodica

ELECTROPHILE-INITIATED LACTONIZATION
1711
Table 1. 1H NMR spectra of lactones IVa and IVd IVf in CDCl3, , ppm
Compound no.
3-H
2-H, 4-H
2.01 2.19
1-H, 5-H
3.63 br.s
3.56 br.s
Ph
Other protons
IVa
IVd
1.16 1.37
1.51 1.69
1.18 1.37
1.66 1.83
7.34 7.43 (2H)
7.43 7.55 (3H)
7.25 7.40 (5H)
7.40 7.50 (3H)
7.60 7.72 (2H)
7.24 7.35 (2H)
7.38 7.50 (3H)
7.24 7.41 (2H)
7.42 7.56 (3H)
7.32 7.55 (5H)
1.91 2.06
2.06 2.24
IVe (X = OAc)
IVe (X = Br)
IVea (X = Cl)
IVf
1.43 1.60
1.71 1.92
1.44 1.62
1.64 1.83
1.13 1.29
1.54 1.72
1.40 1.60
1.95 2.20
1.97 2.19
3.78 br.s
3.84 br.s
3.67 br.s
3.60 br.s
2.08 s (CH3)
1.75 1.91
2.05 2.23
1.85 2.00
2.00 2.15
7.18 7.37 (2H)
7.37 7.53 (3H)
3.01 s (6-H)
a
In DMSO-d6.
Table 2. 13C NMR spectra of lactones IVa and IVd IVf in CDCl3, C, ppm
Compound no.
C3
C2, C4 C1, C5
C6
C7
C O [CH3]
Ph
IVa
IVd
13.8
14.3
21.8
21.1
62.2
59.6
61.4
61.2
88.9
89.0
170.8
174.6
127.2, 129.0, 130.0, 131.5
127.0, 128.0, 128.8, 128.85, 129.7,
130.3, 132.0, 133.2
IVe (X = OAc)
IVe
15.0
15.0
14.8
15.6
24.1
23.8
23.7
22.8
64.0
64.1
63.6
57.7
67.3
74.8
74.6
46.0
94.2
93.8
93.3
92.0
177.8, 178.9 127.7, 129.1, 129.7, 131.5
[23.1]
178.3
179.1
177.1
127.3, 128.8, 129.5, 130.9
127.7, 129.0, 129.4, 132.5
127.9, 128.8, 129.4, 130.6
IVea (X = Cl)
IVf
a
In DMSO-d6.
intermediate norpinane cation A which is generated by
strictly endo-selective [7] attack by electrophile E+
on the C1 atom of acid III. The reaction is completed
by intramolecular nucleophilic attack by the carboxy
group on the cationic center (Scheme 2).
The structure of newly synthesized lactones IVd,
1
IVe, IVf was convincingly proved by the H and
13C NMR spectra (Tables 1 and 2); for comparison,
the data for previously described bromo lactone IVa
are also given.
Scheme 2.
E = PhS (d), HgX (e), H (f).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 12 2003

1712
RAZIN, ZOLOTAREV
Scheme 3.
Unlike hydrogen chloride, the other reagents giving
synthesis and is confirmed by spectral data. The
vicinal coupling constant of the 7-H proton, J = 4.9
5.7 Hz, indicates exo-configuration of molecules V,
VIII, IX, and X [9].
rise to electrophilic hydrogen species induced more
profound transformations of the tricycloheptane
skeleton of initial acid III. For example, in the pres-
ence of a catalytic amount of sulfuric acid in dioxane
compound III underwent isomerization into acid V
having a norcarane skeleton. When gaseous hydrogen
iodide was passed through a solution of acid III in
methylene chloride, two products were formed at
a ratio of 11:2. Among these, only the minor product
was the expected lactone IVf. The major product,
lactone VI, was also synthesized by reaction of III
with chlorotrimethylsilane in the presence of NaI and
water. Presumably, the system Me3SiCl/NaI/H2O
generates hydrogen iodide which initiates the above
transformation of acid III. Obviously, the reaction
path leading to acid V includes intermediate formation
of norcaranyl cation B. The latter is also precursor of
VI. As shown in Scheme 3, cation B reacts with HI
to give iodo-substituted acid VII which is reduced to
VIII, and lactonization of VIII yields final product
VI. Cation B is formed as a result of the known cyclo-
butyl cyclopropylcarbinyl isomerization of cation A
(E = H). Taking into account the steric structure of A
and stereospecificity of the isomerization [8], the
carboxy group in cation B and acids V, VII, and
VIII should be oriented exo. The last stage in the
formation of lactone VI (Scheme 3) was proved by
direct lactonization of acid VIII which was obtained
by independent synthesis via carbene reaction of
1-phenylcyclohexene with ethyl diazoacetate. Acids
V and VIII were treated with diazomethane to obtain
the corresponding methyl ethers IX and X. The struc-
1
The H and 13C NMR spectra of lactone VI are
consistent with the proposed structure: a characteristic
chemical shift of the C1 atom ( 88.2 ppm) may be
noted as an example. cis-JunctCion of the bicyclic
skeleton of VI was assumed on the basis of the result
of lactonization of the methyl analog of VIII, reported
previously [4].
EXPERIMENTAL
1
The H and 13C NMR spectra were recorded on
a Bruker DPX-300 spectrometer operating at 300.13
and 75.47 MHz, respectively; CDCl3 or DMSO-d6
was used as solvent. Elemental analysis was per-
formed on an HP 185B CHN-analyzer. Silufol UV-
254 plates were used for analytical TLC. The products
were separated and purified by column chromatog-
raphy on silica gel L 40/100 m (Chemapol). Bis-
(benzonitrile)dichloropalladium(II) [11] and benzene-
sulfenyl chloride [12] were prepared by known
methods. 7-Phenyltricyclo[4.1.0.02,7]heptane-1-car-
boxylic acid (III), mp 168 C, was synthesized by the
procedure reported in [3].
6-Bromo-7-phenylbicyclo[3.1.1]heptane-6,7-car-
bolactone (IVa). A solution of 0.49 g (1 mmol) of
bromomercurio lactone IVe (X = Br) in 15 ml of
methylene chloride was added to a solution of 0.32 g
(2 mmol) of bromine in 20 ml of methylene chloride.
The mixture was stirred for 10 h and treated with
water. The organic phase was separated, washed with
a solution of sodium thiosulfate and with water, and
dried over anhydrous sodium sulfate. The solvent
was removed to leave 0.28 g (96%) of lactone IVa,
1
ture of V and IX was proved by the H and 13C
NMR spectra. Specifically, the multiplicity of signals
belonging to the olefinic protons is typical of 2-nor-
carene derivatives [9]. The structure of VIII and X
unambiguously follows from the procedure of their
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ELECTROPHILE-INITIATED LACTONIZATION
1713
mp 116 C; published data [3]: mp 116 C; Rf 0.55
(hexane ether, 1:1).
42.12; H 3.58, 3.63. C14H13ClHgO2. Calculated, %:
C 42.06; H 3.53.
7-Phenylbicyclo[3.1.1]heptane-6,7-carbolactone
(IVf). a. A solution of HCl in methylene chloride,
0.5 ml (obtained by shaking a mixture of methylene
chloride with hydrochloric acid and subsequent drying
over CaCl2), was added to a solution of 2.14 g
(10 mmol) of acid III in 20 ml of methylene chloride.
The mixture was stirred for 3 h at room temperature,
the solvent was removed under reduced pressure, the
residue was diluted with 30 ml of diethyl ether, and
the ether solution was washed with a 5% aqueous
solution of sodium hydrogen carbonate and with
water, dried over anhydrous sodium sulfate, and
evaporated to obtain 2.03 g (95%) of lactone IVf.
b. Dry hydrogen chloride was passed over a period
of 2 h through a suspension of 0.45 g (1 mmol) of
lactone IVe (X = Cl) in 30 ml of carbon tetrachloride.
An aqueous solution of sodium acetate was then
added, and the organic phase was separated, washed
with water, and dried over anhydrous sodium sulfate.
Removal of the solvent left 0.12 g (55%) of IVf.
c. Bis(benzonitrile)dichloropalladium(II), 19.2 mg,
(1 mmol), was added to a solution of 1.07 g (5 mmol)
of acid III in 20 ml of acetonitrile, and the mixture
was stirred for 50 h under reflux in an argon atmos-
phere. The mixture was then filtered through a 2-cm
layer of silica gel, the solvent was removed from
the filtrate under reduced pressure, and the residue
was purified by flash chromatography on silica gel
using hexane methylene chloride (2:1) as eluent.
Yield of IVf 0.37 g (35%).
d. Azobis(isobutyronitrile), 25 mg, was added to
440 mg (1.5 mmol) of lactone IVa and 495 mg
(1.7 mmol) of tributylstannane in 30 ml of anhydrous
benzene, and the mixture was heated for 7 h under
reflux, a 10 15-mg portion of AIBN being added
every 1.5 h. The product was purified by column
chromatography. Yield 151 mg (47%). mp 76 C
(from hexane). Rf 0.48 (hexane ether, 1:1). Found,
%: C 78.46, 78.45; H 6.58, 6.56. C14H14O2. Calcu-
lated, %: C 78.48; H 6.59.
7-Phenyl-6-phenylsulfanylbicyclo[3.1.1]heptane-
6,7-carbolactone (IVd). A flask was charged under
argon with 1.07 g (5 mmol) of acid III, 0.57 g
(5.6 mmol) of triethylamine, and 10 ml of methylene
chloride. The flask was capped with a septum, the
mixture was cooled to 25 C, and a solution of 1.01 g
(7 mmol) of benzenesulfenyl chloride in 10 ml of
methylene chloride was added using a syringe over
a period of 10 min under stirring. The mixture was
stirred for 1 h at 25 C and for 3 h at room tempera-
ture. The solvent was removed under reduced pres-
sure, 20 ml of benzene was added to the residue, and
the solution was filtered. Purification by column
chromatography gave 1.41 g (86%) of lactone IVd.
mp 97 C (hexane). Rf 0.52 (hexane ether, 2:1).
Found, %: C 74.42, 74.54; H 5.60, 5.67. C20H18O2S.
Calculated, %: C 74.50; H 5.63.
Reaction of acid III with mercury acetate.
Mercury acetate, 5.58 g (18 mmol), was added to
a solution of 3.21 g (15 mmol) of acid III in 75 ml
of methylene chloride, and the mixture was stirred
for 24 h. Water, 80 ml, was added, and the organic
phase was separated, washed with water (3 30 ml),
and dried over anhydrous sodium sulfate. Yield of
6-acetoxymercurio-7-phenylbicyclo[3.1.1]heptane-
6,7-carbolactone (IVe, X = OAc) 5.98 g (85%).
mp 117 C (from methanol ether). Found, %: C 40.86,
40.88; H 3.51, 3.54. C16H16HgO4. Calculated, %:
C 40.64; H 3.41. A solution of 0.24 g (2 mmol) of
potassium bromide in 7 ml of water was added to
a solution of 0.95 g (2 mmol) of compound IVe
(X = OAc) in 5 ml of methanol. The resulting suspen-
sion was stirred for 4 h at room temperature and
diluted with 5 ml of water, and 30 ml of chloroform
was added. The organic phase was separated, and
the aqueous phase was extracted with chloroform
(3 10 ml). The extracts were combined with the
organic phase, washed with water, and dried over
anhydrous sodium sulfate. Removal of the solvent left
0.93 g (94%) of 6-bromomercurio-7-phenylbicyclo-
[3.1.1]heptane-6,7-carbolactone (IVe, X = Br).
mp 129 C (from chloroform). Found, %: C 34.16,
34.18; H 2.69, 2.71. C14H13BrHgO2. Calculated, %:
C 34.06; H 2.65.
1-Phenylbicyclo[4.1.0]hept-2-ene-exo-7-car-
boxylic acid (V). Concentrated sulfuric acid, 50 mg,
was added to a solution of 0.214 g (1 mmol) of acid
III in 7 ml of dioxane, and the mixture was stirred
for 50 h at room temperature. The solution was
neutralized with 2 g of powdered barium carbonate,
the solvent was evaporated, and the residue was
recrystallized to obtain 0.175 g (85%) of acid V.
Likewise, from 0.95 g (2 mmol) of lactone IVe
(X = OAc) in 5 ml of methanol and 7 ml of a solution
of sodium chloride (0.12 g, 2 mmol) in water we
obtained 0.83 g (83%) of 6-chloromercurio-7-phenyl-
bicyclo[3.1.1]heptane-6,7-carbolactone (IVe, X = Cl).
mp 125 C (from chloroform). Found, %: C 42.07,
mp 105 C (from hexane). 1H NMR spectrum
(DMSO-d6), , ppm: 1.79 1.96 (2H, 5-H), 2.05 2.20
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 12 2003

1714
RAZIN, ZOLOTAREV
(2H, 4-H), 2.23 d (1H, 7-H, J = 5.7 Hz), 2.52 br.s
(1H, 6-H), 5.60 d.d (1H, 3-H, J = 9.9, 7.1 Hz), 5.99 d
(1H, 2-H, J = 9.9 Hz), 7.19 7.38 (5H, Ph), 10.78 (1H,
CO2H). 13C NMR spectrum (DMSO-d6), C, ppm:
17.2, 19.8, 27.3, 32.0, 36.0, 124.4, 126.7, 128.2 (2C),
128.7 (2C), 131.7, 140.7, 176.2 (C O). Found, %:
C 78.42, 78.44; H 6.60, 6.61. C14H14O2. Calculated,
%: C 78.48; H 6.59.
water and dried over anhydrous magnesium sulfate.
After removal of the solvent, the residue (0.25 g)
was a mixture of lactones IVf and VI at a ratio of
1
2:11 (according to the H NMR data).
1-Phenylbicyclo[4.1.0]heptane-exo-7-carboxylic
acid (VIII). A solution of 8 g (0.07 mol) of ethyl
diazoacetate in 5 ml of octane was added over a period
of 1 h with stirring under nitrogen to a mixture of
15.8 g (0.1 mol) of 1-phenylcyclohexene and 50 mg
of anhydrous copper sulfate in 10 ml of octane, heated
to 125 C. When the addition was complete, the mix-
ture was heated for an additional 10 min (until
nitrogen no longer evolved). The mixture was cooled,
8 g of potassium hydroxide in 150 ml of ethanol was
added, and the mixture was heated for 3 h under
reflux with stirring, cooled, and diluted with 300 ml
of water. Volatile organic substances were removed
by steam distillation, and the still residue was con-
centrated to a volume of 100 ml and acidified to
pH 1 by adding dilute sulfuric acid on cooling. The
precipitate was filtered off and repeatedly recrystal-
lized from aqueous methanol. Yield of acid VIII 2.1 g
Methyl 1-phenylbicyclo[4.1.0]hept-2-ene-exo-7-
carboxylate (IX) was synthesized by treatment of
acid V with a solution of diazomethane in diethyl
1
ether. H NMR spectrum (CDCl3), , ppm: 1.81 2.0
(2H), 2.08 2.25 (2H), 2.32 d (1H, 7-H, J = 5.6 Hz),
2.59 2.64 (1H), 3.44 s (3H, OCH3), 5.61 d.d.d
(1H, 3-H, J = 9.7, 7.0, 1.4 Hz), 6.03 d (1H, 2-H, J =
9.7 Hz), 7.22 7.38 (5H, Ph). 13C NMR spectrum
(CDCl3), C, ppm: 17.2, 19.9, 26.5, 32.2, 34.8, 51.2
(OCH3), 124.1, 126.2, 128.2 (2C), 128.7 (2C), 131.9,
141.1, 170.6 (C O).
6-Phenyl-7-oxabicyclo[4.3.0]nonan-8-one (VI).
a. Freshly distilled chlorotrimethylsilane (bp 57 C),
0.12 g (1.1 mmol), sodium iodide, 0.15 g (1 mmol),
and water, 18 mg (1 mmol), were added to a solution
of 0.21 g (1 mmol) of acid III in 25 ml of benzene.
The mixture was stirred for 10 h, washed with a solu-
tion of sodium thiosulfate and with water, and dried
over anhydrous magnesium sulfate. After removal
of the solvent, the residue was purified by flash
chromatography on silica gel using hexane methylene
chloride (6:1) as eluent. Yield 0.17 g (78%). Oily
substance, Rf 0.64 (hexane methylene chloride, 6:1).
1H NMR spectrum (CDCl3), , ppm: 1.26 1.54 (2H),
1.55 1.71 (2H), 1.72 1.85 (2H), 1.92 2.25 (1H),
2.13 d (1H, J = 16.4 Hz) and 2.42 d.d (1H, J =
16.4, 6.7 Hz) (7-CH2), 2.17 2.27 (1H), 2.63 2.74
(1H, 6-H), 7.22 7.48 (5H, Ph). 13C NMR spectrum
(CDCl3), C, ppm: 21.6, 23.6, 29.2, 37.4, 37.6, 40.4,
1
(14%). mp 181 C. H NMR spectrum (DMSO-d6),
, ppm: 1.15 1.31 (2H), 1.32 1.48 (2H), 1.60 1.76
(2H), 1.83 d (1H, 7-H, J = 5.1 Hz), 1.95 2.03 (3H),
2.05 2.22 (2H), 7.10 7.32 (5H, Ph), 11.71 br.s (1H,
CO2H). 13C NMR spectrum (DMSO-d6), C, ppm:
21.55, 21.65, 23.0, 24.6, 32.1, 34.0, 36.4, 126.8,
128.9 (2C), 129.1 (2C), 145.4, 173. Found, %:
C 77.57, 77.82; H 7.54, 7.37. C14H16O2. Calculated,
%: C 77.75; H 7.46.
Methyl 1-phenylbicyclo[4.1.0]heptane-exo-7-car-
boxylate (X) was synthesized by treatment of acid
VIII with a solution of diazomethane in ether.
1H NMR spectrum (CDCl3), , ppm: 1.25 1.55 (4H),
1.74 1.91 (2H), 1.93 d (1H, 7-H, J = 4.9 Hz), 2.12
2.30 (3H), 3.43 s (3H, OCH3), 7.17 7.34 (5H, Ph).
13C NMR spectrum (CDCl3), C, ppm: 21.0, 21.05,
22.5, 24.7, 31.7, 33.0, 36.6, 51.1 (OCH3), 126.1,
128.0 (2C), 128.1 (2C), 144.2, 172.2 (C O).
88.2 (C1), 125.1 (2C), 128.0, 128.9 (2C), 144.7, 177.6
(C O). Found, %: C 77.66, 77.69; H 7.49, 7.56.
C14H16O2. Calculated, %: C 77.75; H 7.46.
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(1 mmol) of acid VIII in 25 ml of benzene. The sub-
sequent procedure was the same as described above
in a. Yield of VI 0.18 g (81%).
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hydrogen iodide was passed over a period of 1 h
through a solution of 0.21 g (1 mmol) of acid III
in 30 ml of methylene chloride. The solution was
washed in succession with a solution of sodium thio-
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