Mendeleev Commun., 2018, 28, 644–645
O
O
temperature (20°C, 30 days), which could explain the low yield
(27%) of lactones 12a,b.
1
4
O
In summary, we have demonstrated that pentafluoroperbenzoic
acid is a promising and efficient Baeyer–Villiger reagent highly
competitive with traditional mCPBA.
HO
HO
5
6, 81%
Scheme 3 Reagents and conditions: C F CO H (1.5 equiv.), MoO(O ) ·2QOH
6
5
3
2 2
(
5 mol%), CH Cl –C H Cl , 20°C, 6 h.
This work was carried out within the framework of the State
Assignment (no. AAAA-A17-117012610063-8). The authors are
grateful to the Regional Center for Collective Use ‘Agidel’ for
the provided equipment.
2
2
2
4
2
allowed us to increase the yield of lactone 6 up to 81% at the full
conversion of 5 (Scheme 3).
To estimate the PFPBA opportunites as the versatile oxidizer,
cycloalkanones C –C and C 7a–e were tested. The reaction was
Online Supplementary Materials
5
8
12
processed at the twofold excess of PFPBA providing the cor-
responding lactones 8a–e (Scheme 4). High yields of lactones
Supplementary data associated with this article can be found
in the online version at doi: 10.1016/j.mencom.2018.11.027.
8c–e were achieved under the conditions of 50°C and 12 h. In the
oxidation of cyclopentanone 7a, the yield of 5-pentanolide 8a did
not exceed 50% due to the formation of side 5-hydroxypentanoic
acid. Note that to achieve high yields of lactones 8a–e using
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mCPBA, a prolonged exposure at 20°C for 5 days and 70°C for
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O
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C
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b
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40
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93
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catalyst gives single regioisomer 10a of two possible (Scheme 5).
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presence of 5 mol% of the catalyst, while in the absence of the
catalyst it was 67%. The analogous oxidation with mCPBA is
1
1 U. M. Dzhemilev, N. S. Vostrikov, A. M. Moiseenkov and G. A. Tolstikov,
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1
9
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1
3 R. I. Khusnutdinov and T. M. Oshnyakova, Russ. J. Org. Chem., 2015,
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5
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1
4 R. I. Khusnutdinov, T. M Oshnyakova, L. M. Khalilov, A. R. Baibuldina
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R
R
R
R
R
R
R
R
R
O
O
O
+
O
O
9
, 11
10a, 12a
10b, 12b
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2
C F CO H [Mo]
Yield
(%)
6
5
3
Solvent T/°C t/h Products
R
H
(
equiv.)
(mol%)
5
J. Chem. Soc., Perkin Trans. 1, 1991, 1793.
9
1
1.5
CH2Cl2– 20
C2H4Cl2
6 10a
94
1
Me 2
–
CH2Cl2 40 20 12a + 12b 40
1 : 2.5)
(
Scheme 5
Received: 10th May 2018; Com. 18/5571
–
645 –