Reaction of bulky organosilicon compounds with CS2: Cleavage and rearrangement reactions of 1,2-epoxides

Journal of Organometallic Chemistry 762 (2014) 29e33

Contents lists available at ScienceDirect

Journal of Organometallic Chemistry journal homepage: www.elsevier.com/locate/jorganchem

Reaction of bulky organosilicon compounds with CS2: Cleavage and rearrangement reactions of 1,2-epoxides Kazem D. Safa*, Khatereh Ghorbanpour, Mahsa Ebrahiminia Organosilicon Research Laboratory, Faculty of Chemistry, University of Tabriz, 51664 Tabriz, Iran

a r t i c l e i n f o

a b s t r a c t

Article history: Received 4 November 2013 Received in revised form 30 January 2014 Accepted 25 February 2014

The reaction of tris(trimethylsilyl)methyllithium, (Me3Si)3CLi, and carbon disulfide with various epoxides have been studied. By an unusual rearrangement hydroxy-mercaptobis-(trimethylsilyl)-thiones have been synthesized in good yields. Unexpectedly, in the case of 2-phenyloxirane two structural isomers (2g) and (2h) have been formed which was confirmed by IR, 1H and 13C NMR spectroscopy. Moreover, the reaction of (PhMe2Si)3CLi and (Me3Si)3CLi with CS2 in the presence of epoxides has been compared. Ó 2014 Published by Elsevier B.V.

Keywords: Tris(trimethylsilyl)methyllithium Tris(dimethylphenylsilyl)methyllithium Organosilicon Organosulfur Carbon disulfide

Introduction Despite of many research publications during the past decade about the applications of organosilicon chemistry to synthesis, there are few simple available reagents based upon silicon chemistry that can be used to conduct useful synthetic transformations [1,2]. We have pursued a program of research that utilizes simple and readily available organosilicon reagents to carry out synthetic transformations [3e7]. In recent years, the bulky reagents [(RMe2Si)3CLi (R ¼ H, Me, Ph)] have been used in various reactions such as the preparation of vinylsilanes, epoxysilanes, halovinylsilanes, silyl ethers and, etc [8e 11]. Then a novel, efficient and quantitative preparation of a variety of multifunctional mercaptobis-(trimethylsilyl)-thiones from the reaction of tris(trimethylsilyl)methyllithium ((Me3Si)3CLi) and carbon disulfide with benzyl, alkyl and allyl halides have been described by unusual rearrangement of (Me3Si)3CLi with carbon disulfide [12,13]. In addition, the chemistry of carbon disulfide has been studied extensively [14e18] especially, the reaction of amines with carbon disulfide that cause to formation of dithiocarbamates, is well known [19e24]. On the other hand, the treatment of organosilyl compounds with carbon disulfide is less known [25e27] so the investigations of the treatment of (RMe2Si)3CLi with carbon disulfide were started in the presence of different electrophiles and

* Corresponding author. Tel.: þ98 411 3393124; fax: þ98 411 3340191. E-mail address: [email protected] (K.D. Safa). http://dx.doi.org/10.1016/j.jorganchem.2014.02.019 0022-328X/Ó 2014 Published by Elsevier B.V.

developed ways of making carbonecarbon and carbonesulfur bonds mediated by silicon reagents. With this in mind, we have examined the reactions of (RMe2Si)3CLi (R ¼ Me, Ph) and carbon disulfide with epoxides in an effort to synthesize new hydroxy-mercaptobis-(trimethylsilyl)-thiones that can play an important role to synthesize hydroxythio derivatives as useful intermediates and building blocks in organic chemistry. Results and discussion As reported in the previous publications [12,13], mercaptobis(trimethylsilyl)-thiones (1) were prepared by using bulky tris(trimethylsilyl)methyllithium (Me3Si)3CLi, carbon disulfide and various halides such as alkyl iodides, allyl and benzyl bromides. These reactions took place at 46  C in a short period of time (Scheme 1). To extend our investigations to organosilicon compounds, the reactions of (Me3Si)3CLi with CS2 were studied in the presence of epoxides. Initially, the reaction of (Me3Si)3CLi and CS2 with 2methyloxirane was chosen as model reaction for optimization (Table 1). This model reaction was carried out in different temperatures and times. The best temperature was found to be 5  C. The results are listed in Table 1. As shown in Table 1, at 5  C the mixture of materials was stirred for 15 min and compound 2a was formed in 80% (Entry 3) but at 46  C (cyclohexanon/N2) and 94  C (hexane/N2) no reaction took place. The prolong reaction time (Entry 4) and elevated

30

K.D. Safa et al. / Journal of Organometallic Chemistry 762 (2014) 29e33 Table 2 Reaction of (Me3Si)3CLi and CS2 with various epoxides

Scheme 1. Reaction of (Me3Si)3CLi and CS2 with alkyl, allyl and benzyl halides.

reaction temperature (Entry 5) resulted in lower yields of 2a due to the formation of unidentified decomposition products. To explore the versatility of this reaction, the reaction of (Me3Si)3CLi and CS2 with various epoxides was carried out at 5  C. The results are summarized in Table 2. (Me3Si)3CLi and CS2 underwent a specific rearrangement with a variety of epoxides at 5  C to give the corresponding hydroxymercaptobis-(trimethylsilyl)-thions in good yields (Table 2). All of the synthesized compounds (2), through this route have been structurally confirmed by 1H NMR, 13C NMR, GCeMS and IR spectroscopy. In the IR spectrum, a broad peak was observed at 3400e 3555 cm1 for OH and in the 1H NMR spectrum, there were two broad peaks at 2.06 and 3.16 ppm that justified the presence of OH and SH groups. In the reaction of (Me3Si)3CLi and CS2 with cyclic epoxides (Entries 9 and 10) no products were formed, but in the reaction with 2-(allyloxymethyl)oxirane (Entry 8) many unidentified compounds were formed that the separation of them was unsuccessful. In the reaction of (Me3Si)3CLi, CS2 and 2-phenyloxirane (Entry 7), there were differences in the spectroscopic data. In the IR spectrum for the resulted compound, not only there was OH peak in 3455 cm1, but also a strong peak was observed at 1739 cm1 that presents C]O group. In addition, 1H NMR and 13C NMR confirmed the formation of two compounds as shown in Scheme 2. According to spectroscopic data and several publications illustrating intramolecular or intermolecular oxygenesulfur exchange [12,13,17,26,28e30], the mechanism of the formation of 2g [12,13] and 2h have been proposed as shown in Scheme 3. The structural elucidation of compound 2h revealed that oxygenesulfur exchange in compound 2g has been occurred. We postulated that oxygene sulfur exchange has been carried out via E to K intermediates. The attempts to isolate these compounds and indicate them separately were unsuccessful. However, spectroscopic data show two compounds (structural isomers) were formed approximately in ratio 50:50. In a logical extension of the studies, the bulky tris(dimethylphenylsilyl)methyllithium (PhMe3Si)3CLi, was used instead of

Table 1 Investigation of temperature effects on the reaction of (Me3Si)3CLi, CS2 and 2methyloxirane.

Temperature ( C)

Time (min)

(2a)a (%)

1 2 3 4 5

94 46 5 5 25

15 15 15 60 15

e e 80 50 e

Yields were obtained by PTLC.

Product

Timea Yieldb (min) (%)

1

15

80

2

15

75

3

15

70

4

15

70

5

20

72

6

30

65

7

60

70

8

e

120

e

9

-

120

e

10

e

120

e

a

Entry

a

Entry Epoxide

b

End of the reaction was followed by TLC. Yields obtained by PTLC.

(Me3Si)3CLi and compared their reaction with CS2 in the presence of epoxides. (PhMe2Si)3CLi exhibits low and unusual reactivity toward (Me3Si)3CLi because of the severe steric hindrance produced at the centers to which they are attached [9]. It was envisaged that

K.D. Safa et al. / Journal of Organometallic Chemistry 762 (2014) 29e33

31

Scheme 2. Formation of compounds 2g and 2h from the reaction of (Me3Si)3CLi, CS2 and 2-phenyloxirane.

the reaction of (PhMe2Si)3CLi and CS2 with 2-methyloxiran would give rise to hydroxyl-mercaptobis-(trimethylsilyl)-thiones (2). However, contrary to our expectation, the desired compound 2 was not obtained, and surprisingly, the major product was found to be

known cyclic thiocarbonate 3 [31] (Scheme 4). This reaction was quantitatively carried out at 0  C in 15 min. One of the most efficient methods for synthesizing cyclic thiocarbonates is the reaction of epoxide with carbon disulfide in

Scheme 3. The proposed mechanisms of the reaction of (Me3Si)3CLi and CS2 with epoxides. The mechanism of the formation of (a) 2g and (b) 2h.

32

K.D. Safa et al. / Journal of Organometallic Chemistry 762 (2014) 29e33

Scheme 4. Reaction of (PhMe2Si)3CLi and CS2 with 2-methyloxiran.

catalyst systems [31e33]. Likely, in our reaction (PhMe2Si)3CLi activates the CS2 to react with the epoxide for the formation of cyclic thiocarbonate 3.

evaporated and the residue was purified by preparative TLC on silica gel using n-hexane: ethyl acetate 6:1 as eluent to give the product.

Conclusion

4-Hydroxy-1-mercapto-1,1-bis(trimethylsilyl)pentane-2-thione (2a) A yellow liquid, 80% (Rf ¼ 0.20, n-hexane: ethyl acetate 17:3). FTIR (KBr, cm1): 3387 (OH), 2960 (CH), 1404 (C]S), 1250, 918 and 839 (CeSi), 1150 (CeS), 1026 (CeO); 1H NMR (400 MHz, CDCl3): d 0.15 (s, 18H, SiMe3), 1.27 (d, J ¼ 6.2 Hz, 3H, CH3), 2.06 (b.s, 1H, OH), 3.17 (b.s, 1H, SH), 3.22e3.30 (dd, J ¼ 13.9 Hz and 7.0 Hz, 1H, CH2), 3.42e3.46 (dd, J ¼ 13.9 Hz and 4.2 Hz, 1H, CH2), 3.99e4.06 (m, 1H, CHOH); 13C NMR (CDCl3): d 0.96 (SiMe3), 21.45 (CH3), 44.22 (CH2), 55.88 (C(SiMe3)2SH), 65.80 (CHOH), 203.62 (C]S); Anal. Calcd for C11H26OS2Si2: C, 44.8; H, 8.9; S, 21.8. Found: C, 45.1; H, 8.6; S, 21.8%.

In this work, a novel, efficient and quantitative preparation of a variety of multifunctional hydroxy-mercapto-bis(trimethylsilyl)thiones have been described from the reaction of (Me3Si)3CLi and CS2 with epoxides in THF at 5  C. In the case of 2-phenyloxirane two structural isomers were synthesized. Moreover, the presented results show that (PhMe2Si)3CLi exhibits unusual reactivity to that of (Me3Si)3CLi because of severe steric hindrance and unexpectedly cyclic thiocarbonate were generated. Experimental Solvents and reagents The reactions were carried out under dry argon. Solvents and CS2 were dried by standard methods. Substrates for the preparation of (Me3Si)3CLi and (PhMe2Si)3CLi, viz. Me3SiCl (Merck), PhMe2SiCl (Merck), PhBr (Merck), n-BuLi (Merck), Li (Merck), MeI (Merck), CHCl3 (Merck), CHBr3 (Merck), and substrate for the preparation of hydroxy-mercaptobis-(trimethylsilyl)-thiones, viz. epoxides (Merck) were used as received.

4-Hydroxy-1-mercapto-1,1-bis(trimethylsilyl)hexane-2-thione (2b) A yellow liquid, 75% (Rf ¼ 0.50, n-hexane: CH2Cl2 1:1), FTIR (KBr, cm1): 3421 (OH), 2960 (CH), 1404 (C]S), 1250, 919 and 839 (Ce Si), 1148 (CeS), 1021 (CeO); 1H NMR (400 MHz, CDCl3): d 0.15 (s, 18H, SiMe3), 0.98 (t, 3H, CH3), 1.52e1.61 (m, 2H, CH2), 2.06 (b.s, 1H, OH), 3.16 (b.s, 1H, SH), 3.22e3.27 (dd, J ¼ 13.9 Hz and 7.5 Hz, 1H, CH2), 3.45e3.50 (dd, J ¼ 14.0 Hz and 3.7 Hz, 1H, CH2), 3.70e3.75 (m, 1H, CHOH); 13C NMR (CDCl3): d 1.23 (SiMe3), 8.93 (CH3), 28.55 and 42.61 (CH2), 55.82 (C(SiMe3)2SH), 70.96 (CHOH), 203.62 (C]S); Anal. Calcd for C12H28OS2Si2: C, 46.7; H, 9.1; S, 20.8. Found: C, 46.4; H, 9.2; S, 20.9%.

Spectra The 1H NMR and 13C NMR were recorded with a Bruker FT400MHz spectrometer at room temperature and CDCl3 as a solvent. The FTIR spectra were recorded on a Bruker-Tensor 270 spectrometer. Elemental analyses were obtained with a Vario EL III instrument. The mass spectra were obtained with a GCeMS Agilent, quadrupole mode 5973N instrument, operating at 70 eV. All of the compounds decomposed during GCeMS analysis to give fragments with m/z (EI): 235 ([HSC(SiMe3)2C]S]þ), 203 ([HSCC(SiMe3)2]þ), 163 ([HSCC(SH)SiMe3]þ), 115 ([HSCCSiMe2]þ), 73 ([SiMe3]þ). Preparation of tris(trimethylsilyl)methyllithium ((Me3Si)3CLi) and tris(dimethylphenylsilyl)methyllithium ((PhMe2Si)3CLi) The reagents were prepared as described according to the literature methods [1,9]. Typical procedure for the preparation of hydroxyl-mercaptobis(trimethylsilyl)-thiones (2a-2g) To a stirred solution of tris(trimethylsilyl)methyllithium (1 mmol) in THF, carbon disulfide (1.2 mmol) in 2 ml THF was added at 5  C under argon atmosphere. The mixture was stirred for 5 min and then epoxide (1 mmol) was added at this temperature and the stirring was maintained to the end of the reaction that followed by TLC. The mixture was poured into cold water and extracted with CH2Cl2. The organic layer was washed with HCl (5 N) then brine, dried with Na2SO4 and filtered. The solvent was

4-Hydroxy-1-mercapto-1,1-bis(trimethylsilyl)heptane-2-thione (2c) A yellow liquid, 70% (Rf ¼ 0.40, n-hexane: CH2Cl2 1:1), FTIR (KBr, cm1): 3450 (OH), 2957 (CH), 1374 (C]S), 1250, 919 and 839 (CeSi), 1148 (CeS), 1022 (CeO); 1H NMR (400 MHz, CDCl3): d 0.15 (s, 18H, SiMe3), 0.95 (t, 3H, CH3), 1.34e1.40 (m, 2H, CH2), 1.54e1.61 (m, 2H, CH2), 2.06 (b.s, 1H, OH), 3.17 (b.s, 1H, SH), 3.22e3.27 (dd, J ¼ 13.9 Hz and 7.3 Hz, 1H, CH2), 3.45e3.50 (dd, J ¼ 14.0 Hz and 3.8 Hz, 1H, CH2), 3.80e3.82 (m, 1H, CHOH); 13C NMR (CDCl3): d 1.18 (SiMe3), 11.20 (CH3), 25.71, 35.40, 43.12 (CH2), 55.88 (C(SiMe3)2SH), 70.06 (CHOH), 203.80 (C]S); Anal. Calcd for C13H30OS2Si2: C, 48.4; H, 9.4; S, 19.9. Found: C, 48.7; H, 9.2; S, 19.8%. 4-Hydroxy-1-mercapto-1,1-bis(trimethylsilyl)octane-2-thione (2d) A yellow liquid, 70% (Rf ¼ 0.33, n-hexane: CH2Cl2 1:1), FTIR (KBr, cm1): 3455 (OH), 2957 (CH), 1374 (C]S), 1250, 919 and 840 (CeSi), 1148 (CeS), 1024 (CeO); 1H NMR (400 MHz, CDCl3): d 0.15 (s, 18H, SiMe3), 0.90 (t, 3H, CH3), 1.33e1.40 (m, 4H, 2  CH2), 1.54e1.60 (m, 2H, CH2), 2.06 (b.s, 1H, OH), 3.17 (b.s, 1H, SH), 3.22e3.27 (dd, J ¼ 13.9 Hz and 7.3 Hz, 1H, CH2), 3.45e3.50 (dd, J ¼ 14.0 Hz and 3.8 Hz, 1H, CH2), 3.81e3.82 (m, 1H, CHOH); 13C NMR (CDCl3): d 1.18 (SiMe3), 13.00 (CH3), 21.62, 26.71, 35.40, 43.12 (CH2), 55.88 (C(SiMe3)2SH), 69.96 (CHOH), 209.12 (C]S); Anal. Calcd for C14H32OS2Si2: C, 49.9; H, 9.6; S, 19.0. Found: C, 49.7; H, 9.8; S, 19.1%. 4-Hydroxy-5-isopropoxy-1-mercapto-1,1-bis(trimethylsilyl) pentane-2-thione (2e) A brown liquid, 72%: (Rf ¼ 0.33, n-hexane: ethyl acetate 17:3), FTIR (KBr, cm1): 3448 (OH), 2970 (CH), 1375 (C]S), 1250, 919 and

K.D. Safa et al. / Journal of Organometallic Chemistry 762 (2014) 29e33

840 (CeSi), 1147 (CeS), 1088 and 1023 (CeO); 1H NMR (400 MHz, CDCl3): d 0.14 (s, 18H, SiMe3), 1.15 (d, J ¼ 5.9 Hz, 6H, 2  CH3), 2.06 (b.s, 1H, OH), 3.16 (b.s, 1H, SH), 3.30e3.31 (dd, J ¼ 6.8 Hz, 1H, CH2), 3.34e3.36 (dd, J ¼ 6.4 Hz and 2.5 Hz, 1H, CH2), 3.43e3.48 (dd, J ¼ 14.5 Hz and 4.8 Hz, 1H, CH2), 3.51e3.55 (dd, J ¼ 9.2 Hz and 3.5 Hz, 1H, CH2), 3.56e3.65 (m, 1H, CH(CH3)2), 3.94e3.95 (m, 1H, CHOH); 13C NMR (CDCl3): d 1.18 (SiMe3), 21.00 (CH3), 43.12 (CH2), 55.88 (C(SiMe3)2SH), 69.96 (CHOH), 74.95 (CH2O), 76.11 (CHO), 209.29 (C]S); Anal. Calcd for C14H32O2S2Si2: C, 47.7; H, 9.1; S, 18.2. Found: C, 48.1; H, 9.1; S, 18.1%. 5-Chloro-4-hydroxy-1-mercapto-1,1-bis(trimethylsilyl)pentane-2thione (2f) A brown liquid, 65% (Rf ¼ 0.62 n-hexane: ethyl acetate 17:3), FTIR (KBr, cm1): 3450 (OH), 2970 (CH), 1375 (C]S), 1250, 919 and 840 (CeSi), 1146 (CeS), 1087 and 1023 (CeO); 1H NMR (400 MHz, CDCl3): d 0.15 (s, 18H, SiMe3), 2.06 (b.s, 1H, OH), 3.17 (b.s, 1H, SH), 3.45e3.51 (dd, J ¼ 19.0 Hz and 4.4 Hz, 1H, CH2), 3.57e3.61 (dd, J ¼ 11.0 Hz and 5.9 Hz, 1H, CH2), 3.67e3.78 (m, 2H, CH2Cl), 4.06e 4.08 (m, 1H, CHOH); 13C NMR (CDCl3): d 1.23 (SiMe3), 35.95 (CH2Cl), 47.50 (CH2), 56.10 (C(SiMe3)2SH), 69.40 (CHOH), 209.29 (C]S); Anal. Calcd for C11H25ClOS2Si2: C, 40.1; H, 7.7; S, 19.5. Found: C, 39.6; H, 7.9; S, 19.8%. 4-Hydroxy-1-mercapto-4-phenyl-1,1-bis(trimethylsilyl)butane-2thione (2g) and 1,4-dimercapto-4-phenyl-1,1-bis(trimethylsilyl) butan-2-one (2h) A brown liquid, 70% (2g ¼ 50.6% and 2h ¼ 49.4%, 2g/2h ratio have been calculated by (CH) of CHOH and (CH) of CHSH integrations in the 1H NMR spectrum) (Rf ¼ 0.5, n-hexane: CH2Cl2 1:1), FTIR (KBr, cm1): 3455 (OH), 3030 (CHAr), 2957 (CH), 1739 (C] O), 1373 (C]S), 1250, 917 and 842 (CeSi), 1149 (CeS), 1057 (CeO); 1 H NMR (400 MHz, CDCl3): d 0.15 (s, 18H, SiMe3)g, 0.21 (s, 18H, SiMe3)h, 2.59 (b.s, 1H, OH)g, 2.82 (b.s, 1H, SH)h, 2.84e2.91 (m, 1H, CH2)h, 2.93 (s, 1H, SH)h, 3.10e3.14 (dd, J ¼ 6.6 Hz and 3.1 Hz, 1H, CH2)h, 3.21 (b.s, 1H, SH)g, 3.43e3.49 (dd, J ¼ 14.0 Hz and 8.5 Hz, 1H, CH2)g,, 3.75e3.79 (dd, J ¼ 14.0 Hz and 3.1 Hz, 1H, CH2)g, 4.98e4.99 (m, 1H, CHSH)h, 5.03e5.06 (m, 1H, CHOH)g, 7.29e7.49 (m, 10H, 2  Ar)g and h; 13C NMR (CDCl3): d 1.17 (SiMe3), 43.45 and 44.63 (CH2)g and h, 56.00 (C(SiMe3)2SH)g and h, 71.22 (CHSH), 71.65 (CHOH), 124.73e141.61 (2  Ar)g and h. Reaction of (PhMe2Si)3CLi and CS2 with 2-methyloxirane and formation of compound (3) To a stirred solution of (PhMe2Si)3CLi (1 mmol) in THF, carbon disulfide (1.2 mmol) was added at 0  C under an argon atmosphere. The mixture was stirred for 5 min and then 2-methyloxirane (1 mmol) was added at this temperature and the stirring was maintained as the mixture was allowed to end of the reaction. The progress of the reaction was followed by TLC with n-hexane and ethyl acetate 9:1 as solvent. The reaction was finished in 15 min. Then the mixture was poured into water and extracted with CH2Cl2. The organic layer was washed with water, dried with Na2SO4 and filtered. The solvent was evaporated from the filtrate and the residue was purified by preparative TLC on silica gel with n-hexane:ethyl acetate 9:1 as eluent. Colorless liquid, 80% (Rf ¼ 0.28), 1H

33

NMR (400 MHz, CDCl3): d 1.59 (d, J ¼ 6.2 Hz, 3H, CH3), 3.31e3.39 (dd, J ¼ 9.9 Hz, 1H, CH2), 3.59e3.64 (dd, J ¼ 11.0 Hz and 6.5 Hz, 1H, CH2), 5.16e5.25 (m, 1H, CH); 13C NMR (CDCl3): d18.04 (CH3), 39.61 (CH2), 86.96 (CH), 213.62 (C]S). Acknowledgment We thank financial support of this work by the Iran National Science Foundation (INSF) and Tabriz University is gratefully appreciated. Appendix A. Supplementary data Supplementary data related to this article can be found at http:// dx.doi.org/10.1016/j.jorganchem.2014.02.019. References [1] L. Fleming, C.D. Floyd, J. Chem. Soc. Perkin Trans. 1 (1981) 969e976. [2] F. Cooke, R. Moerck, J. Schwindeman, P. Magnus, J. Org. Chem. 45 (1980) 1046e1053. [3] K.D. Safa, M. Shahrivar, S. Tofangdarzadeh, A. Hassanpour, Tetrahedron 63 (2007) 3189e3194. [4] K.D. Safa, F. Mosleh, P. Kalantarzadeh, Phosphorus, Sulfur Silicon 178 (2003) 1261e1268. [5] K.D. Safa, H.A. Eram, M.H. Nasirtabrizi, Iran. Polym. J. 15 (2006) 249e257. [6] K.D. Safa, O. Rafigh, M.H. Nasirtabriiz, J. Chem. Res. 5 (2006) 379e383. [7] K.D. Safa, M. Babazadeh, J. Organomet. Chem. 690 (2005) 79e83. [8] K.D. Safa, K. Ghorbanpour, A. Hassanpour, S. Tofangdarzadeh, J. Organomet. Chem. 694 (2009) 1907e1911. [9] K.D. Safa, A. Hassanpour, S. Tofangdarzadeh, M.H. Nasirtabrizi, J. Iran. Chem. Soc. 5 (2008) 458e463. [10] K.D. Safa, S.P. Samani, S. Tofangdarzadeh, A. Hassanpour, J. Organomet. Chem. 693 (2008) 2004e2008. [11] K.D. Safa, M. Namvari, A. Hassanpour, S. Tofangdarzadeh, J. Organomet. Chem. 694 (2009) 2448e2453. [12] K.D. Safa, K. Ghorbanpour, J. Organomet. Chem. 745e746 (2013) 214e218. [13] K.D. Safa, K. Ghorbanpour, J. Sulfur Chem. 35 (2014) 170e178. [14] A.D. Dunn, W.D. Rudorf, Carbon Disulphide in Organic Chemistry, Ellis Horwood Limited, Chichester, 1989, pp. 1e389. [15] S.R. Ramadas, P.S. Srinivasan, J. Ramachandran, V.V.S.K. Sastry, Synthesis (1983) 605e622. [16] S. Kato, M. Ishida, J. Sulfur Chem. 8 (1988) 155e312. [17] W.D. Rudorf, Sulfur Rep. 11 (1991) 51e141. [18] O. Niyomura, S. Kato, Top. Curr. Chem. 251 (2005) 1e12. [19] N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei, M.R. Saidi, J. Org. Chem. 71 (2006) 3634e3635. [20] F. Kardon, M. Mortl, G. Magyarfalvi, Synth. Commun. 38 (2008) 192e199. [21] A. Alizadeh, N. Zohreh, H. Sabahnoo, Z. Noaparast, Tetrahedron 67 (2011) 1709e1715. [22] N. Lal, L. Kumar, A. Sarswat, S. Jangir, V.L. Sharma, Org. Lett. 13 (2011) 2330e 2333. [23] N. Azizi, B. Pourhasan, F. Aryanasab, M.R. Saidi, Synlett 8 (2007) 1239e1242. [24] A. Ziyaei-Halimjani, M.R. Saidi, Can. J. Chem. 84 (2006) 1515e1519. [25] A. Alizadeh, S. Rostamnia, N. Zohreh, R. Hosseinpour, Tetrahedron Lett. 50 (2009) 533e1535. [26] A. Ehlend, H.D. Hausen, W. Kaim, A. Lichtblau, W. Schwarz, J. Organomet. Chem. 501 (1995) 283e292. [27] D. Seyferth, R.C. Hui, Tetrahedron Lett. 25 (1984) 2623e2626. [28] A. Wright, D. Ling, P. Boudjouk, R. West, J. Am. Chem. Soc. (1972) 4784e4785. [29] K. Takeda, K. Sumi, S. Hagisawa, J. Organomet. Chem. 611 (2000) 449e454. [30] A. Guigne, P. Metzner, Phosphorus, Sulfur Silicon 25 (1985) 97e102. [31] L. Bo, Z. Zhi-Chao, Z. Ying-Ju, J. Kun, L. Xiao-Bin, in: Proceedings of the Third Conference on Functional Molecules, 2005, pp. 119e124. [32] J.A. Durden, H.A. Stansbury, W.H. Catlette, J. Am. Chem. Soc. 82 (1960) 3082e 3084. [33] M.V. Jesudason, L.N. Owen, J. Chem. Soc. Perkin Trans. 1 (1974) 1443e1446.