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A facile method for the synthesis of novel imidoyl iminosulfuranes from imidoyl azides
Tetrahedron Letters 55 (2014) 5892–5894
Contents lists available at ScienceDirect
Tetrahedron Letters journal homepage: www.elsevier.com/locate/tetlet
A facile method for the synthesis of novel imidoyl iminosulfuranes from imidoyl azides Fahimeh Movahedifar, Ali Reza Modarresi-Alam ⇑, Behzad Hosseinzadeh Department of Chemistry, University of Sistan & Baluchestan, Zahedan, Iran
a r t i c l e
i n f o
Article history: Received 14 January 2014 Revised 28 August 2014 Accepted 11 September 2014 Available online 21 September 2014
a b s t r a c t A novel and environmentally friendly method for the one-pot preparation of new imidoyl iminosulfuranes in high yield under microwave (MW) and solvent-free conditions from the corresponding imidoyl azides is presented. This efficient synthetic approach benefits from non-toxic and non-explosive precursors for the synthesis of imidoyl iminosulfuranes. Ó 2014 Elsevier Ltd. All rights reserved.
Keywords: Imidoyl azides Imidoyl iminosulfuranes Microwave (MW) Solvent-free reaction
Sulfur–nitrogen ylides (also called sulfilimines, sulfilimides, iminosulfuranes) have proved to be important reagents in organic synthesis, particularly in reactions involving intermolecular attack on substrates bearing an electrophilic carbon atom. A wide range of applications have been reported based on their inherent biological activities.1,2 In the process of sulfilimine synthesis, sulfoxides are undesirable by-products, which affect the sulfilimine yield. Most described procedures for sulfide to sulfonyl sulfilimine transformation use a broad range of sulfonyl nitrenoid sources known as chloramine salts (R3SO2NClNa),2 and iron-catalyzed or NBS-mediated nitrogen transfer reactions.3 Moreover, the thermal or photochemical transfer of nitrenes from an azide to the sulfur atom in a sulfide or sulfoxide results in sulfilimines and sulfoximides, respectively.4 Because of the difficulties involved in liberating nitrenes, however, the yields of these processes are low. Iron(II) chloride was reported to facilitate the synthetic efficiency of this process by reducing the reaction temperature from 90 °C to 0 °C.5 Morita and coworkers introduced dibenzothiophene sulfilimines as useful sources for the generation of nitrenes by photolysis of N-substituted iminodibenzothiophene.6 Recently, imidoyl azides have been used as convenient precursors for the generation of nitrenes.7 However, harsh conditions are involved in the generation of nitrenes since most azides suffer from problems such as handling difficulties, risks of explosion, and low selectivity which also leads ⇑ Corresponding author. Tel.: +98 9153414338. E-mail address: [email protected] (A.R. Modarresi-Alam). http://dx.doi.org/10.1016/j.tetlet.2014.09.062 0040-4039/Ó 2014 Elsevier Ltd. All rights reserved.
to low yields.8–10 Imidoyl azides, by contrast, show none of these problems.7 Furthermore, there is no need to use transition metals such as iron salts. The imidoyl group (ArAOAC@NAY) has been used in order to control the stability of the azide and to increase the selectivity of the reactive nitrene.7 In connection with the synthetic value of sulfilimines, we report herein a simple and efficient synthesis of new aryloxyimidoyl sulfilimines. Although Lwowski and Rao prepared dimethyl sulfoximines by imination of DMSO with imidoyl nitrenes,11 to the best of our knowledge however, there has been no report on the use of imidoyl azides for the synthesis of sulfilimines. The imidoyl sulfilimines 3 were readily prepared in high yields by the reaction between imidoyl azides 2 and methyl phenyl sulfide under microwave irradiation and solvent-free conditions, Scheme 1 and Table 1. Imidoyl azides 2 were prepared from the corresponding tetrazoles 1, and these were prepared from phenols by a previously described general method.7 The products were characterized from their spectroscopic data (IR, 1H NMR, and 13C NMR spectra), elemental analysis (CHNS), and melting points. In the IR spectra of compounds 3, no bands were observed in the region corresponding to the azide group. Asymmetric and symmetric SO2 stretches appeared at 1200–1365 cm1 and 1040–1180 cm1, respectively. Stretching vibrations of the S@N bond typically appeared at 920–980 cm1 with various substituents on the nitrogen and sulfur atoms.1,12 However, a decrease in the frequencies of the stretching vibrations of the S@N bond with increasing electron-withdrawing acceptor ability of the substituents on the nitrogen atom led to a red shift from the above
5893
F. Movahedifar et al. / Tetrahedron Letters 55 (2014) 5892–5894
H N O Ar
N
N N
N Ar'SO2Cl Et 3N, EtOAc
O Ar 2
1
SO 2Ar'
N3
S
Ph
CH3
Ar
O N
MW (1-5 min), solvent-f ree
3
N
SO 2Ar'
S
CH3
Ph
a: Ar = 3-MeC6H4, Ar' = 4-MeC6H4, b: Ar = 3-MeC6H4, Ar' = 4-BrC6H4, c: Ar = 4-MeC6H4, Ar' = 4-MeC6H4, d: Ar = 4-MeC6H4, Ar' = C6H5, e: Ar = 3-MeC6H4, Ar' = C6H5 Scheme 1.
Table 1 Synthesis of iminosulfuranes 3 from aryloxy imidoyl azides 2 and methyl phenyl sulfide Entry
1
Substrate
Product
O N O S O N3
H3C
O N S O
CH3
H 3C
Yield (%)
Melting point (°C)
90
124–126
87
150–152
89
133–135
91
186–187
92
145–147
CH3
O N
S CH3
2a
3a O N O S O N3 2
O N S O
CH3
Br
Br
CH3
O N
S CH3
2b
3b O N O S O N3 3
CH 3
H3 C
O N S O
H 3C
N O S O N3
4
CH3
N
S CH3
2c O
O
3c
CH3
O N S O
O CH3
N
S
2d
CH3
3d O N O S O N3
CH3
O N S O
5
O N
S
2e
CH3
CH3
3e
mentioned values to 800–900 cm1 in N-acyl sulfilimines such as R2S@NCOAR. Since there were no peaks in this region for compounds 3 and, on the other hand, because of the high conjugation of the imidoyl group (ArOAC@NASO2Ar), which results in an increase in the electron-withdrawing acceptor ability, we attributed the absorption in the region of 850–895 cm1 to the stretching vibration of the S@N bond in compounds 3. In the 1H NMR spectra, the protons of the methyls attached to the sulfur atom, the ArAOA aromatic ring, and the ArASO2A aromatic ring appeared at 2.8–2.9 ppm, 2.30 ppm, and 2.39 ppm, respectively. The same methyls occurred at 36 ppm and 21 ppm in the 13C NMR spectra. The signals at 162.5 ppm, 150–153 ppm, 141–143 ppm, and 139–141 ppm are attributed to the carbon atom of the imidoyl group (ArAOAC@NAY), and the ipso carbon atoms of
ArAOA, Ar0 ASO2A, and PhAS@NAY, respectively. The 13C NMR spectra and CHNS analyses clearly proved the presence of an imidoyl sulfilimine group. We also applied diallyl sulfide, a structurally analogous sulfide, to test whether 2,3-allylic rearrangement8,13 into the isomeric N,S-diallyl benzenesulfenamide 3g from the corresponding iminosulfurane 3f would occur (Scheme 2). In order to synthesize the desired product, the same procedure was carried out as mentioned above. The final product was a black solid material that was insoluble in organic solvents and water. Minor by-products were eliminated by preparative TLC. The rearrangement product was not present according to NMR spectroscopy. We suggest that diallyl sulfide (4), under these conditions, undergoes polymerization. In fact, the formation of soluble and linear polymers or insoluble and cross-linked polymers from
5894
F. Movahedifar et al. / Tetrahedron Letters 55 (2014) 5892–5894
N O Ar
N3
2
Ar
SO2Ar'
O
N
MW (1-5 min), solvent-f ree
S 4
SO 2Ar'
Ar
O
N
SO2Ar'
N
N S
S
(m) cm1. 1H NMR (500 MHz, CDCl3), d ppm; 2.29 (s, 3H), 2.39 (s, 3H), 2.85 (s, 3H), 6.66 (s, 1H), 6.69 (d, J = 8.1 Hz, 1H), 6.96 (d, J = 7.4 Hz, 1H), 7.14 (t, J = 7.8 Hz, 1H), 7.19 (d, J = 7.9 Hz, 2H), 7.51 (t, J = 7.6 Hz, 2H), 7.57–7.59 [m (d+t), 3H], 7.81 (d, J = 8.0 Hz, 2H). 13 C NMR (125 MHz, CDCl3), d ppm; 162.43, 152.82, 141.35, 141.01, 139.02, 134.17, 132.74, 130.09, 128.63, 128.53, 127.40, 126.73, 126.07, 122.18, 118.72, 36.09, 21.40, 21.21. Anal. calcd. For C22H22N2O3S2: C 61.95, H 5.20, N 6.57, S 15.03; found: C 61.56, H 5.11, N 6.43, S 14.92.
3g 3f
Acknowledgment
Scheme 2.
diallyl sulfides can take place depending on the polymerization conditions.14,15 Furthermore, it has been reported that products of dimerization of thioacrolein obtained from pyrolysis of diallyl disulfide 4 can be polymerized.16 In addition, ring-forming polymerization is also possible from 3f and 3g.14 In summary, we have developed a novel, efficient, and mild protocol for the one-pot preparation of new iminosulfuranes from precursor imidoyl azides and methyl phenyl sulfide under MW irradiation and solvent-free conditions. The advantages of the present method in terms of facile manipulation, high yields, simple methodology, simple work-up procedure, no chromatographic separation, and fast reaction rates should make this protocol a valuable alternative to existing methods. Further studies are in progress. Typical procedure for the preparation of imidoyl iminosulfuranes 3 A mixture of imidoyl azide 2a–e (1.0 mmol) and methyl phenyl sulfide (1.3 mmol) in a beaker was irradiated at 800 W using a Milestone Microwave (Microwave Labstation) for 1–5 min. The progress of the reaction was monitored by TLC. After completion of the reaction, petroleum ether was added and a crude red product was obtained. The product was recrystallized from EtOAc–petroleum ether to give pure 3a–e. 3-Methylphenyl-N-[(4-methylphenyl)sulfonyl]-N0 -(methylphenylsulfuranylidene)imidocarbamate (3a) Yield 90%, white crystals, mp 124–126 °C. IR (KBr); 3085 (vw), 2950 (vw), 1604 (vw), 1496 (vs), 1442 (w), 1429 (w), 1396 (vw), 1364 (s), 1358 (s), 1273 (m), 1243 (m), 1164 (m), 1139 (s), 1098 (m), 1070 (m), 1016 (w), 976 (w), 932 (w), 909 (w), 881 (s), 806 (m), 785 (m), 737 (m), 717 (s), 684 (m), 660 (m), 604 (s), 553
We gratefully acknowledge the financial support from the Research Council of the University of Sistan and Baluchestan. Supplementary data Supplementary data associated with this article can be found, in the online version, at http://dx.doi.org/10.1016/j.tetlet.2014.09. 062. References and notes 1. Gilchrist, T. L.; Moody, C. J. Chem. Rev. 1977, 77, 409. 2. Marzinzik, A. L.; Sharpless, K. B. J. Org. Chem. 2001, 66, 594. 3. (a) Mancheno, O. G.; Dallimore, J.; Plant, A.; Bolm, C. Adv. Synth. Catal. 2010, 352, 309; (b) Mancheno, O. G.; Bistri, O.; Bolm, C. Org. Lett. 2007, 9, 3809; (c) Cho, G. Y.; Bolm, C. Tetrahedron Lett. 2005, 46, 8007. 4. (a) Ando, W.; Ogino, N.; Migita, T. Bull. Chem. Soc. Jpn. 1971, 44, 2278; (b) Ando, W.; Yagihara, T.; Kondo, S.; Nakayama, K.; Yamato, H.; Nakaido, S.; Migita, T. J. Org. Chem. 1971, 36, 1732. 5. (a) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015; (b) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033. 6. Morita, H.; Tatami, A.; Maeda, T.; Kim, B. J.; Kawashima, W.; Yoshimura, T.; Abe, H.; Akasaka, T. J. Org. Chem. 2008, 73, 7159. 7. (a) Dabbagh, H. A.; Lwowski, W. J. Org. Chem. 1989, 54, 3952; (b) Dabbagh, H. A.; Lwowski, W. J. Org. Chem. 2000, 65, 7284; (c) Dabbagh, H. A.; Ghaelee, S. J. Org. Chem. 1996, 62, 3439; (d) Dabbagh, H. A.; Modarresi-Alam, A. R. J. Chem. Res. (S) 2000, 190; (e) Dabbagh, H. A.; Modarresi-Alam, A. R. J. Chem. Res. (S) 2000, 44; (f) Dabbagh, H. A.; Karimzadeh, R. Molecules 2002, 7, 189; (g) Dabbagh, H. A.; Modarresi-Alam, A. R.; Tadjarodi, A.; Taeb, A. Tetrahedron 2002, 58, 2621; (h) Modarresi-Alam, A. R.; Khamooshi, F.; Rostamizadeh, M.; Keykha, H.; Nasrollahzadeh, M.; Bijanzadeh, H.-R.; Kleinpeter, E. J. Mol. Struct. 2007, 841, 61; (i) Modarresi-Alam, A. R.; Keykha, H.; Khamooshi, F.; Dabbagh, H. A. Tetrahedron 2004, 60, 1525. 8. Driver, T. G. Org. Biomol. Chem. 2010, 8, 3831. 9. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188. 10. Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 351. 11. Lwowski, W.; Rao, S. Tetrahedron Lett. 1980, 21, 727. 12. Zabolotnaya, T. G.; Egorov, Y. P.; Levchenko, E. S.; Dubinina, T. N. Theor. Exp. Chem. 1983, 19, 29. 13. Reggelin, M. Top. Curr. Chem. 2007, 275, 1. 14. Cotter, R.; Matzner, M. Ring-Forming Polymerizations Pt B 2: Heterocyclic RingsPart 2; Academic Press, 1972. pp 339–340. 15. Ingsdorf, H.; Overberger, C. G. J. Polym. Sci. 1962, 61, S11. 16. Block, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 1135.
Contents lists available at ScienceDirect
Tetrahedron Letters journal homepage: www.elsevier.com/locate/tetlet
A facile method for the synthesis of novel imidoyl iminosulfuranes from imidoyl azides Fahimeh Movahedifar, Ali Reza Modarresi-Alam ⇑, Behzad Hosseinzadeh Department of Chemistry, University of Sistan & Baluchestan, Zahedan, Iran
a r t i c l e
i n f o
Article history: Received 14 January 2014 Revised 28 August 2014 Accepted 11 September 2014 Available online 21 September 2014
a b s t r a c t A novel and environmentally friendly method for the one-pot preparation of new imidoyl iminosulfuranes in high yield under microwave (MW) and solvent-free conditions from the corresponding imidoyl azides is presented. This efficient synthetic approach benefits from non-toxic and non-explosive precursors for the synthesis of imidoyl iminosulfuranes. Ó 2014 Elsevier Ltd. All rights reserved.
Keywords: Imidoyl azides Imidoyl iminosulfuranes Microwave (MW) Solvent-free reaction
Sulfur–nitrogen ylides (also called sulfilimines, sulfilimides, iminosulfuranes) have proved to be important reagents in organic synthesis, particularly in reactions involving intermolecular attack on substrates bearing an electrophilic carbon atom. A wide range of applications have been reported based on their inherent biological activities.1,2 In the process of sulfilimine synthesis, sulfoxides are undesirable by-products, which affect the sulfilimine yield. Most described procedures for sulfide to sulfonyl sulfilimine transformation use a broad range of sulfonyl nitrenoid sources known as chloramine salts (R3SO2NClNa),2 and iron-catalyzed or NBS-mediated nitrogen transfer reactions.3 Moreover, the thermal or photochemical transfer of nitrenes from an azide to the sulfur atom in a sulfide or sulfoxide results in sulfilimines and sulfoximides, respectively.4 Because of the difficulties involved in liberating nitrenes, however, the yields of these processes are low. Iron(II) chloride was reported to facilitate the synthetic efficiency of this process by reducing the reaction temperature from 90 °C to 0 °C.5 Morita and coworkers introduced dibenzothiophene sulfilimines as useful sources for the generation of nitrenes by photolysis of N-substituted iminodibenzothiophene.6 Recently, imidoyl azides have been used as convenient precursors for the generation of nitrenes.7 However, harsh conditions are involved in the generation of nitrenes since most azides suffer from problems such as handling difficulties, risks of explosion, and low selectivity which also leads ⇑ Corresponding author. Tel.: +98 9153414338. E-mail address: [email protected] (A.R. Modarresi-Alam). http://dx.doi.org/10.1016/j.tetlet.2014.09.062 0040-4039/Ó 2014 Elsevier Ltd. All rights reserved.
to low yields.8–10 Imidoyl azides, by contrast, show none of these problems.7 Furthermore, there is no need to use transition metals such as iron salts. The imidoyl group (ArAOAC@NAY) has been used in order to control the stability of the azide and to increase the selectivity of the reactive nitrene.7 In connection with the synthetic value of sulfilimines, we report herein a simple and efficient synthesis of new aryloxyimidoyl sulfilimines. Although Lwowski and Rao prepared dimethyl sulfoximines by imination of DMSO with imidoyl nitrenes,11 to the best of our knowledge however, there has been no report on the use of imidoyl azides for the synthesis of sulfilimines. The imidoyl sulfilimines 3 were readily prepared in high yields by the reaction between imidoyl azides 2 and methyl phenyl sulfide under microwave irradiation and solvent-free conditions, Scheme 1 and Table 1. Imidoyl azides 2 were prepared from the corresponding tetrazoles 1, and these were prepared from phenols by a previously described general method.7 The products were characterized from their spectroscopic data (IR, 1H NMR, and 13C NMR spectra), elemental analysis (CHNS), and melting points. In the IR spectra of compounds 3, no bands were observed in the region corresponding to the azide group. Asymmetric and symmetric SO2 stretches appeared at 1200–1365 cm1 and 1040–1180 cm1, respectively. Stretching vibrations of the S@N bond typically appeared at 920–980 cm1 with various substituents on the nitrogen and sulfur atoms.1,12 However, a decrease in the frequencies of the stretching vibrations of the S@N bond with increasing electron-withdrawing acceptor ability of the substituents on the nitrogen atom led to a red shift from the above
5893
F. Movahedifar et al. / Tetrahedron Letters 55 (2014) 5892–5894
H N O Ar
N
N N
N Ar'SO2Cl Et 3N, EtOAc
O Ar 2
1
SO 2Ar'
N3
S
Ph
CH3
Ar
O N
MW (1-5 min), solvent-f ree
3
N
SO 2Ar'
S
CH3
Ph
a: Ar = 3-MeC6H4, Ar' = 4-MeC6H4, b: Ar = 3-MeC6H4, Ar' = 4-BrC6H4, c: Ar = 4-MeC6H4, Ar' = 4-MeC6H4, d: Ar = 4-MeC6H4, Ar' = C6H5, e: Ar = 3-MeC6H4, Ar' = C6H5 Scheme 1.
Table 1 Synthesis of iminosulfuranes 3 from aryloxy imidoyl azides 2 and methyl phenyl sulfide Entry
1
Substrate
Product
O N O S O N3
H3C
O N S O
CH3
H 3C
Yield (%)
Melting point (°C)
90
124–126
87
150–152
89
133–135
91
186–187
92
145–147
CH3
O N
S CH3
2a
3a O N O S O N3 2
O N S O
CH3
Br
Br
CH3
O N
S CH3
2b
3b O N O S O N3 3
CH 3
H3 C
O N S O
H 3C
N O S O N3
4
CH3
N
S CH3
2c O
O
3c
CH3
O N S O
O CH3
N
S
2d
CH3
3d O N O S O N3
CH3
O N S O
5
O N
S
2e
CH3
CH3
3e
mentioned values to 800–900 cm1 in N-acyl sulfilimines such as R2S@NCOAR. Since there were no peaks in this region for compounds 3 and, on the other hand, because of the high conjugation of the imidoyl group (ArOAC@NASO2Ar), which results in an increase in the electron-withdrawing acceptor ability, we attributed the absorption in the region of 850–895 cm1 to the stretching vibration of the S@N bond in compounds 3. In the 1H NMR spectra, the protons of the methyls attached to the sulfur atom, the ArAOA aromatic ring, and the ArASO2A aromatic ring appeared at 2.8–2.9 ppm, 2.30 ppm, and 2.39 ppm, respectively. The same methyls occurred at 36 ppm and 21 ppm in the 13C NMR spectra. The signals at 162.5 ppm, 150–153 ppm, 141–143 ppm, and 139–141 ppm are attributed to the carbon atom of the imidoyl group (ArAOAC@NAY), and the ipso carbon atoms of
ArAOA, Ar0 ASO2A, and PhAS@NAY, respectively. The 13C NMR spectra and CHNS analyses clearly proved the presence of an imidoyl sulfilimine group. We also applied diallyl sulfide, a structurally analogous sulfide, to test whether 2,3-allylic rearrangement8,13 into the isomeric N,S-diallyl benzenesulfenamide 3g from the corresponding iminosulfurane 3f would occur (Scheme 2). In order to synthesize the desired product, the same procedure was carried out as mentioned above. The final product was a black solid material that was insoluble in organic solvents and water. Minor by-products were eliminated by preparative TLC. The rearrangement product was not present according to NMR spectroscopy. We suggest that diallyl sulfide (4), under these conditions, undergoes polymerization. In fact, the formation of soluble and linear polymers or insoluble and cross-linked polymers from
5894
F. Movahedifar et al. / Tetrahedron Letters 55 (2014) 5892–5894
N O Ar
N3
2
Ar
SO2Ar'
O
N
MW (1-5 min), solvent-f ree
S 4
SO 2Ar'
Ar
O
N
SO2Ar'
N
N S
S
(m) cm1. 1H NMR (500 MHz, CDCl3), d ppm; 2.29 (s, 3H), 2.39 (s, 3H), 2.85 (s, 3H), 6.66 (s, 1H), 6.69 (d, J = 8.1 Hz, 1H), 6.96 (d, J = 7.4 Hz, 1H), 7.14 (t, J = 7.8 Hz, 1H), 7.19 (d, J = 7.9 Hz, 2H), 7.51 (t, J = 7.6 Hz, 2H), 7.57–7.59 [m (d+t), 3H], 7.81 (d, J = 8.0 Hz, 2H). 13 C NMR (125 MHz, CDCl3), d ppm; 162.43, 152.82, 141.35, 141.01, 139.02, 134.17, 132.74, 130.09, 128.63, 128.53, 127.40, 126.73, 126.07, 122.18, 118.72, 36.09, 21.40, 21.21. Anal. calcd. For C22H22N2O3S2: C 61.95, H 5.20, N 6.57, S 15.03; found: C 61.56, H 5.11, N 6.43, S 14.92.
3g 3f
Acknowledgment
Scheme 2.
diallyl sulfides can take place depending on the polymerization conditions.14,15 Furthermore, it has been reported that products of dimerization of thioacrolein obtained from pyrolysis of diallyl disulfide 4 can be polymerized.16 In addition, ring-forming polymerization is also possible from 3f and 3g.14 In summary, we have developed a novel, efficient, and mild protocol for the one-pot preparation of new iminosulfuranes from precursor imidoyl azides and methyl phenyl sulfide under MW irradiation and solvent-free conditions. The advantages of the present method in terms of facile manipulation, high yields, simple methodology, simple work-up procedure, no chromatographic separation, and fast reaction rates should make this protocol a valuable alternative to existing methods. Further studies are in progress. Typical procedure for the preparation of imidoyl iminosulfuranes 3 A mixture of imidoyl azide 2a–e (1.0 mmol) and methyl phenyl sulfide (1.3 mmol) in a beaker was irradiated at 800 W using a Milestone Microwave (Microwave Labstation) for 1–5 min. The progress of the reaction was monitored by TLC. After completion of the reaction, petroleum ether was added and a crude red product was obtained. The product was recrystallized from EtOAc–petroleum ether to give pure 3a–e. 3-Methylphenyl-N-[(4-methylphenyl)sulfonyl]-N0 -(methylphenylsulfuranylidene)imidocarbamate (3a) Yield 90%, white crystals, mp 124–126 °C. IR (KBr); 3085 (vw), 2950 (vw), 1604 (vw), 1496 (vs), 1442 (w), 1429 (w), 1396 (vw), 1364 (s), 1358 (s), 1273 (m), 1243 (m), 1164 (m), 1139 (s), 1098 (m), 1070 (m), 1016 (w), 976 (w), 932 (w), 909 (w), 881 (s), 806 (m), 785 (m), 737 (m), 717 (s), 684 (m), 660 (m), 604 (s), 553
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