Organometallics 1989,8, 2817-2820
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Isolation and Characterization of Tetramethyltellurium( I V ) Robert W. Gedridge, Jr.,* Daniel C. Harris, Kelvin T. Higa, and Robin A. Nissan Chemistry Division, Research Department, NaVal Weapons Center, China Lake, California 93555 Received June 5, 1989
Tetramethyltellurium(IV),Me4Te, was isolated from the reaction of TeC1, with 4.2 equiv of MeLi in ether at -78 "C under argon atmosphere in 77% yield. Me4Te is a malodorous yellow-orange pyrophoric liquid that is stable in the dark under argon atmosphere at 25 "C. It decomposes above 100 "C to give Me2Te,methane, and ethane and is decomposed by intense visible light. The infrared, Raman, and ultraviolet spectra of Me4Te are reported. The 'H-coupled NMR spectrum exhibits a quartet (6 20.6 ppm, 'JT& = 127.8 Hz, 'JC-H = 133.4 Hz) downfield of Me2Te (6 -21.5 ppm). The 'H-coupled I2Te NMR spectrum exhibits a symmetrical multiplet of 11 peaks (6 -67 ppm, 2JTe-H = 34.0 Hz). For comparison, tetravinyltellurium(IV), (CH2=CH),Te, was synthesized from TeCl, and 4.2 equiv of (CH2=CH)MgBr in tetrahydrofuran and characterized by '25Te NMFL Although tetraalkyltellurium(N) compounds are known, they were believed to be unstable and have not been isolated and characterized until now.
Introduction In spite of the malodorous nature, light sensitivity and toxicity' associated with organotellurium compounds, these compounds have a variety of useful applications in organic synthesis2 and semiconductor film growth? Our research has focused on the synthesis and characterization of diorganyltellurium precursors for the pyrolytic and photoassisted metal-organic chemical vapor deposition of mercury cadmium telluride semiconductor films., Diorganyltellurium compounds have been obtained by reducing TeC14 or diorganyl tellurium dihalides (R2TeX2) with Grignard reagents"5 or organolithium reagents." The amount of alkylating reagents used was sufficient to form tetraorganyltellurium(1V) intermediates that readily decompose by reductive elimination to yield the diorganyltellurium(I1) compounds. In support of this mechanism, crystalline tetraaryltellurium(1V) compounds such as (C6H5),Te,' (C6F5),Te? and bis(2,2'-biphenylylene)tellu-
r i u m ( W have been synthesized by using organolithium reagents. (C6H5),Teand bis(2,2'-biphenylylene)tellurium were stable to approximately 140 (in toluene) and 260 "C (under vacuum), respectively, before decomposing to their diaryltellurium analogues. In contrast, tetraalkyl or dialkyl T~, diary1tellurium(1V) compounds such as ( ~ - B u ) ~ Me4Te, and (dimethyl-2,2'-biphenylylene)tellurium have been prepared in solution but never isolated since they readily decomposed to diorganyl tellurides.8b We now report the synthesis and characterization of Me4Te from the reaction of TeC1, with 4.2 equiv of MeLi in ether. Applications of Me4Te in catalysis, coordination chemistry, and chemical vapor deposition and as an oxidizing agent in organic synthesis are currently being explored.
Results and Discussion Preparation and Properties. Me4Te was prepared in 77% yield as described by eq 1. The yellow-orange liquid TeC1,
(1) Browning, E. Toxicity of Industrial Metak, 2nd ed.; Butterworths & Co.: London, 1969; pp 310-316. (2) (a) Irgolic, K. J. The Organic Chemistry of Tellurium; Gordon and Breach Science: New York, 1974. (b) Engman, L. Acc. Chem. Res. 1985, 18, 274. (c) Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1. (d) Suzuki. H.: Hanazaki. Y. Chem. Lett. 1986.549. (e) Suzuki. H.: Manabe. H.; Enokiya, R.; Hkazaki, Y. Chem. Lett. 1986, 1339. '(f).Ohe, K.; Takahasi, H.; Uemura, S.; Sugita, N. J. Org. Chem. 1987,52,4859. (3) (a) Irvine, S. J. C.; Mullin, J. B. J. Cryst. Growth 1981,55,107. (b) Mullin, J. B.; Irvine, S. J. C. J. Vac. Sci. Technol. 1982,21,178. (c) Irvine, S. J. C.; Tunnicliffe, J.; Mullin, J. B. J. Cryst. Growth 1983,65,479. (d) Hoke, W. E.; Lemonias, P. J.; Traczewski, R. Appl. Phys. Lett. 1984,44, 1046. (e) Hoke, W. E.; Lemonias, P. J. Appl. Phys. Lett. 1985,46,398. (f) Morris, B. J. Appl. Phys. Lett. 1986, 48, 867. (g) Hoke, W. E.; Lemonias, P. J. Appl. Phys. Lett. 1986, 48, 1669. (h) Kisker, D. W.; Steigerwald,M. K.; Kometani, T. Y.; Jeffers, K. S. Appl. Phys. Lett. 1987, 50,1681. (i) Irvine, S. J. C.; Mullin, J. B.; Hill, H.; Brown, G. T.; Barnett, S. J. J. Cryst. Growth 1988, 86, 188. 6)Ahlgren, W. L.; Smith, E. J.;
James, J. B.; James, T. W.; Ruth, R. P.; Patten, E. A.; Knox, R. D.; Staudenmann, J.-L. J. Cryst. Growth 1988,86,198. (k) Lichtmann, L. S.; Parsons, J. D.; Cirlin, E.-H. J.Cryst. Growth 1988,86,217. (1) Parsons, J. D.; Lichtmann, L. S. J. Cryst. Growth 1988,86,222. (m) Hoke, W. E.; Lemonias, P. J.; Korenstein, R. J. Mater. Res. 1988,3, 329. (n) Irvine, S. J. C.; Mullin, J. B.; Giess, J.; Gough, J. S.; Royle, A.; Crimes, G. J. Cryst. Growth 1988, 93, 732. ( 0 ) Shenai-Khatkhate, D. V.; Webb, P.; Cole-Hamilton, D. J.; Blackmore, G. W.; Mullin, J. B. J. Cryst. Growth 1988, 93, 744. (p) Hails, J. E.; Irvine, S. J. C.; Mullin, J. B.; ShenaiKhatkhate, D. V.; Cole-Hamilton, D. Mater. Res. SOC. Symp. Proc. 1989, 131, 75. (4) (a) Harris, D. C.; Schwartz, R. W. Mater. Lett. 1986, 4, 370. (b) Harris, D. C.; Nissan, R. A.; Higa, K. T. Inorg. Chem. 1987,26, 765. (c)
Korenstein, R.; Hoke, W. E.; Lemonias, P. J.; Higa, K. T.; Harris, D. C. J.Appl. Phys. 1987,62,4929. (d) Higa, K. T.; Gedridge, R. W.; Harris, D. C. 1st Navy IRIIED Symp. R o c . 1988,1,1. (e) Gedridge, R. W., Jr.; Higa, K. T.; Nissan, R. A. Mater. Res. SOC.Symp. Proc. 1989, 131, 69. (f) Gedridge, R. W., Jr.; Higa, K. T.; Harris, D. C.; Nissan, R. A,; Nadler, M. P. Organometallics, preceding paper in this issue. (9) Higa, K. T.; Harris, D. C. Organometallics 1989, 8, 1674. (5) Jones, C. H. W.; Sharma, R. D. J. Organomet. Chem. 1983,255,
61.
+ 4.2MeLi
ether
Me4Te + 4LiC1
(1)
is stable in the dark under an argon atmosphere a t 25 "C. It decomposes at elevated temperatures or upon exposure to intense light. Me4Te is pyrophoric in air, and on two occasions explosions occurred when it was exposed to air or oxygen. 'H NMR spectroscopy of a dilute toluenedB solution (3% weight) of Me4Te in a sealed tube revealed no decomposition when the sample was heated in the dark a t 94 "C for 30 min. When the sample was heated at 102 "C for 1h, there was approximately 6% conversion to Me2Te. Heating a t 110 "C for another 2 h resulted in 19% conversion to MezTe. Me4Te completely converted to Me2Te after being heated a t 120 "C for 4 h, after which ethane and methane were detected in the NMR spectrum at 0.81 and 0.17 ppm, respectively. Consistent with these observations, distillation of a solution containing (n-Bu),Te resulted in decomposition to (n-Bu)2Te,butane, and octaneaBb 'H NMR. The 'H NMR spectrum of a 2.0 M solution of Me4Te in benzene-d6 displayed a singlet a t 0.99 ppm with a pair of lz5Tesatellite peaks. The methyl protons (6) (a) Wittig, G.; Fritz, H. Justus Liebigs Ann. Chem. 1952,577, 39. (b) Barton, D. H. R.; Glover, S. A.; Ley, S. V. J. Chem. SOC., Chem. Commun. 1977, 266. (c) Glover, S. A. J. Chem. SOC.,Perkin Trans. 1 1980, 1338. (7) Cohen, S. C.; Reddy, M. L. N.; Massey, A. G. J. Orgummet. Chem. 1968, 11, 563. (8)!a) Hellwinkel, D.; Fahrbach, G. Tetrahedron Lett. 1965,1823. (b) Hellwinkel, D.; Fahrbach, G. Chem. Ber. 1968,101,574. (c) Hellwinkel, D.; Fahrbach, G. Justus Liebigs Ann. Chem. 1968,712.1. (d) Hellwinkel, D. Ann. N.Y.Acad. Sci. 1972, 192, 158.
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Figure 1. 63-MHz 'H-coupled l2'?I"eNMR spectrum of MelTe in CBD,. appeared upfield in comparison to those observed for Me2Te (1.83 ~ p m a)t ~a similar concentration in benzene-d,. The singlet for the methyl protons of Me4Te was observed between -90 "C and room temperature. At -90 "C, the sharp singlet shifted 0.06 ppm upfield. The 'H NMR spectrum of bis(4,4'-dimethyl-2,2'-biphenylylene)tellurium also exhibited a single peak for the methyl protons in the range from -55 "C to room temperature.& These observations are inconsistent with a static trigonal-bipyramidal geometry of the four methyl groups and one lone pair of electrons. However, rapid exchange of axial and equitorial groups or a static square-pyramidal geometry with an apical lone pair are consistent with equivalent methyl groups. '3c NMR. The 13C11H)NMR spectrum of Me4Te exhibited a single resonance a t 20.6 ppm with two 12Te satellites, 42.1 ppm downfield from that of MezTe.l0 The l J T 4 coupling for Me4Te (127.8Hz)is significantly smaller than that observed for Me2Te (158Hz)l0 which may be attributed to a decrease in the T e s character of the T e C bonds in Me4Te. The 'H-coupled 13C NMR spectrum of Me,Te displayed a quartet with a slightly smaller coupling constant (4JC-H = 133.4Hz) than that observed for Me2Te (140.7H z ) . ~ 126TeNMR. The 125Te(1H)NMR spectrum of neat Me4Te exhibited a single resonance a t -67 ppm, upfield with respect to neat Me2Te a t 0 ppm. The 'H-coupled 12TeNMR spectrum displayed a symmetrical multiplet with 11 of the expected 13 peaks from coupling to 12 protons (Figure 1) (calculated peak intensity," observed peak intensity): (1,absent), (12,8), (66,64), (220,222),
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Figure 2. 63-MHz partially 'H-coupled ' q e NMR spectrum of (CH.yCH)2Teand (CH2=CH)4Te(with Gaussian resolution
enhancement).
Table I. Vibrational Spectraa Me4Te IRb Ramant Me2Ted MeI' Me2TeBrd 3141 w 2999 w 2967 s 3001 m 3045 w nr 2920 w 2888 s 2921 s 2949 m nr 2838 w 2808 m 2415 w 2423 w 2248 w 1432 m } 1406 m 1417 m 1426 m, br nr 1333 w 1259 w 1221 w 1228 w 1239 w 1210 w 1211 s 1239s 1219 w 1139 w 1073 w 976 w 862 8 876 m ' 08 m } 841 s 839 m 884 m 855 812 w 699 m 623 w 520 w 527 m 523 m u(1-Me) 538 w 507 m 383 s 263 m 219 w 198 185 s 148 s 103 s 98 s
assimta
v,(CH~) v,(CH,)
UcHd
6,(CH3)
CH, rock
u(Te-Me)
6GTe-C)
(495,494),(792,794),(924,924),(792,783),(495,494),(220, 222),(66,66),(12,12),(1,absent). The 'JT,Hcoupling constant for Me4Te (34.0Hz) is larger than that for MeaTe (21.2Hz).', The l25Te{'H) NMR spectrum of a 1 M solution of (CH2=CH),Tel3in C,& exhibited a resonance at 412 ppm. A small amount of (CH,=CH),Te impurity was also observed in this sample a t 534 ppm, in agreement with the reported 530 ppm chemical shift for (CH,=CH),Te in
"Abbreviations: weak (w), medium (m), strong (s), broad (br), no report (nr), symmetric streching (us), asymmetric streching (u,), symmetric bending (&), and asymmetric bending (6=). *4000-450 cm-l. Thin film between KBr plates. c(200-1000 cm-'). Neat liquid in a sealed capillary. d4000-450 cm-'. Thin f i b between KBr plates. Band at 198 cm-I reported in ref 15. e Spectrum of liquid iodomethane above 500 cm-' is from Nicolet/Aldrich Library of Infrared Spectra. Assignmenta are from: Herzberg, G. Infrared and Ramon Spectra of Polyatomic Molecules; Van Nostrand-Reinhold New York, 1945. Spectrum below 550 cm-' was measured in this work using neat liquid in a 0.1 mm pathlength polyethylene cell. There were no bands between 500 and 100 cm-'. fRef. 19.
(9)Pfisterer, G.; Dreeskamp, H. Ber. Bunsenges. Phys. Chem. 1969, 73, 654. (10)Hope, E.G.;Kemmitt, T.; Levason, W. Organometallics 1988,7 , 78. (11)Drago, R. S.Physical Methods in Chemistry; W. B. Saundera Comp.: Philadelphia, 1977; pp 213-214. (12)Schmidt, M.; Block, H. D. Chem. Ber. 1970,103, 3705. (13)(CH,=CH),Te WBB synthesized from the reaction of TeCl, with 4.2 equiv of ( C H 4 H ) M g B r in tetrahydrofuran. Higa, K. T.; Gedridge, R. W., Jr. Organometallics, manuscript in preparation.
CC14.14 The chemical shifts of Me4Te and (CHZ=CH),Te are both upfield with respect to their diorganyl telluride analogue. The 'H-coupled 12Te NMR spectra of (CH2=CH),Te and (CH,=CH),Te displayed complex multiplets due to (14)Kalabin, G.A.; Valeev,R. B.; Kushnarev, D. F. Zh. Org. Khim. 1981,17, 947.
Characterization of Tetramethyltellurium(ZV)
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Figure 3. Fourier transform infrared spectrum of (A) neat M%Te on KBr plates (B) neat Me4Teon KBr plates. coupling of '25Te to the methine and methylene protons. With selective decoupling of the methylene protons, a pentet at 412 ppm and a triplet at 534 ppm (Figure 2) were observed for (CH2=CH),Te and (CH2=CH),Te, respectively. In contrast to the thermal stability of Me4Te, the (CH2=CH),Te sample slowly converted to (CH2=CH)2Te after several hours in the NMR probe at 19 "C with decoupling. IR and Raman Spectra. The infrared spectrum of Me4Te (Figure 3) is compared to those of Me2Te, Me2TeBr2, and Me1 in Table I. Assignment of methyl vibrations is based on normal-coordinate analyses of Me2Te,15Me2Te2,16and MeI.17 For MezTe one absorption in the C-Te stretching region at 527 cm-l is assigned to both symmetric and asymmetric C-Te-C stretching modes, while C-Te-C bending is assigned a t 198 cm-'.15 The structure of Me2TeBr2is expected to be trigonal bipyramidal with a lone pair of electrons in an equatorial position, by analogy to the known crystal structure of Me2TeC12.'* Since C-Te-C bending is observed a t 198 cm-' in Me2Te, we suggest that the band a t 185 cm-' in Me2TeBr2 is due to C-Te-C bending. Asymmetric BrTe-Br stretching is also assigned to this f r e q ~ e n c y . ' ~ Although most C-Te vibrations are observed near 500 cm-', the two C-Te stretching modes of MeTeCWTeMe come at 658 and 219 cm-1.4f In the spectrum of Me2Te in Figure 3, there is no absorption between the CH, rocking modes near 830 cm-l and the C-Te stretching mode at 527 cm-1.15120 In contrast, Me4Te has a prominent band at 699 cm-' and a weak band at 623 cm-', one or both of which could be assigned to C-Te stretching. We were unable to record the far-infrared spectrum of Me4Te (below 500 cm-') because this compound decomposed in polyethylene cells and on KRS-5 plates. However, the Raman spectrum (Figure 4) of a MelTe sample in a glass capillary showed bands at 507,383,263, and 219 cm-'. An additional band a t 519 cm-' had variable intensity in several spectra and was assigned to Me2Te produced by photolysis of Me4Te in the Raman spectrometer. This band was nearly absent in some spectra. Bubble formation in the sample, pre(15) Freeman, J. M.; Henshall, T. J. Mol. Struct. 1967, 1 , 31. (16) Sink, C. W.; Harvey, A. B. J. Mol. Struct. 1969,4, 203. (17) Herzberg, G. Infrared and Raman Spectra of Polyatomic Molecules; Van Nostrand-Reinhold: New York, 1945; p 315. (18) Christofferson, G. D.; Sparks, R. A.; McCullough, J. D. Acta Crystallogr. 1958, 11, 782. (19) Chen, M. T.; George, J. W. J. Am. Chem. SOC.1968, 90,4580. (20) Our spectrum of neat MezTe on KBr plates did not show any bands between 700 and 800 cm-' that had been reported by: Fritz, H. P.; Keller, H. Chem. Ber. 1961, 94, 1524.
WAVENUMBER. cm - 1
Figure 4. Raman spectrum of neat Me,Te in a sealed capillary. The peak at 519 cm-' was of variable intensity in several spectra and is assigned to Me2Te,which may be attributed to the photolysis of Me4Te.
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Figure 5. Ultraviolet spectrum of gas-phase Me4Te at room temperature with a path length of 0.1 mm. Small peaks at 250 and 216 nm (asterisks) are assigned to Me2Te. sumably from the decomposition of Me4Te to Me2Te and alkanes, was increased by increasing laser power and by switching from the 514 nm laser line to the 488 nm laser line. Two possible geometries of Me4Te are trigonal bipyramidal with an equatorial lone pair and square pyramidal with an apical lone pair. Group theory predicts that the C2, trigonal-bipyramidal structure will give rise to four C-Te stretching modes, all of which are infrared- and Raman-active. The C,, square-pyramidal structure gives two infrared-active C-Te stretching modes and three Raman-active modes, two of which should coincide with the infrared modes. Our infrared spectrum shows probable C-Te modes a t 699 and 520 cm-', with another possible band a t 623 cm-'. The region below 500 cm-l was not observed. The Raman spectrum shows no peaks corresponding to the infrared frequencies but has peaks at 507, 383,263, and 219 cm-'. The large number of peaks in the C-Te stretching region is more consistent with the trigonal-bipyramidal structure than the square-pyramidal structure but suggests that more than one structure may be present. Ultraviolet Spectrum. Figure 5 shows the gas-phase ultraviolet spectrum of Me4Te. While the spectra of gaseous dialkyl tellurides such as Me2Te,2' Et2TeZ2and (21) (a) Connor, J.; Greig, G.; Strausz, 0. P. J. Am. Chem. SOC.1969, 91,5695. (b) Scott, J. D.; Causley, G. C.; Russell, B. R. J. Chem. Phys. 1973,59,6577.
2820 Organometallics, Vol. 8, No. 12, 1989
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MesTe at 0 ppm. Infrared spectra were obtained with a Nicolet ( r ~ - B u ) ~ are T e very ~ ~ similar to each other, the spectrum 60-SX Fourier transform spectrometer. All spectra were obtained of Me4Te exhibits broader features. By analogy to the assignments of dialkyl t e l l u r i d e ~ , 2 ~ 3 ~ *at ~ ~4 cm-I resolution by using HappGenzel apodization and a liquid N2 cooled mercury cadmium telluride detector/Ge coated KBr alkyl allyl telluride~,~g and bis(alky1tell~ro)ethynes~~ we beamsplitterfor the 6500-450 cm-' range. A deuterated triglycine assign the shoulder near 290 nm and the broad peak at 263 sulfate detector with a polyethylene window/6.5 pm Mylar nm to n(5p(Te)) a*(Te-C) transitions. The peak at 263 beamsplitter combination was used for the 500-100 cm-' range. nm also includes a 5p,(Te) 6s(Te) Rydberg transition. The Raman spectrum of a liquid sample in a glass capillary tube The broadly rising feature between 238 and 200 nm arises was obtained with a Spex 1-m double monochromator instrument from Me4Te Rydberg transitions from the 5p(Te) orbital using backscattered radiation. The 30 mW Ar+ laser line at 514.5 nm was isolated with a filter and focused to a 0.1 mm spot at the to higher unoccupied T e atomic orbitals. The observation sample. Spectra were the average of two scans recorded with 4 of MezTe impurity in the spectrum of Me4Te may be atcm-' resolution. Ultraviolet-visible spectra were measured with tributed to the photolysis of Me4Te to MezTe in the ula Cary 17D spectrophotometer. traviolet source. Tetramethyltellurium(1V). To a stirring suspension of pulverized TeC1, (10.0 g, 37 mmol) in 40 mL of ether at -78 "C Experimental Section was added dropwise 4.2 equiv of MeLi in ether (1.4 M, 111mL, General Procedures. Organic solvents were distilled under 155mmol). The suspension turned brown initially and then light argon from sodium benzophenone. Synthesis was carried out yellow after the addition was complete. The reaction was warmed under purified Ar by using Schlenk technique^.^^ Air- and to room temperature and stirred 12 h in the dark. The suspension moisture-sensitive materials were transferred inside a He-filled was cooled to -78 "C and filtered to yield a yellow supernatant. Vacuum Atmospheres glovebox. Reaction flasks were wrapped The white precipitate was washed with 25 mL of EhO. The in aluminum foil to minimize exposure to light. Tellurium tetcombined ether solutions were fractionally distilled at 32 "C under rachloride (99%)was purchased from Alfa and pulverized with slight vacuum to remove the solvent. The crude product was a mortar and pestle in the glovebox prior to use. The 1.4 M MeLi collected at -198 "C under vacuum and then purified by vacuum solution in ether and the 1.0 M (CH2=CH)MgBr solution in distillation (45-46 "C, 20 Torr). Pure Me4Tewas obtained as a tetrahydrofuran (THF) were used as received from Aldrich malodorous pyrophoric yellow-orange liquid (5.39 g, 28.7 mmol, Chemical Co. Elemental analyses were performed by Schwankopf 77% yield based on TeC1,). Caution! Pure Me4Teis extremely Microanalytical Laboratories. pyrophoric and sometimes explodes when combined with oxygen. 'H and '9NMR spectra were recorded by using C P , solutions Anal. Calcd for C4H12Te:Te, 67.97. Found: Te, 68.36. A sample with an IBM NR-80 spectrometer operating at 80 or 20 MHz, for C/H analysis exploded upon exposure to oxygen. respectively. l 2 9 eNMR spectra were recorded with a Nicolet Acknowledgment. We gratefully acknowledge finanNT-200-WB spectrometer operating at 63.2 MHz with a 1 0 - r ~ cial support from the Office of Naval Research and a pulse width (corresponding to a 45" flip angle) and a 5-5 receiver delay. 'H-coupled and -decoupled 129eNMR spectra of neat postdoctoral fellowship from the American Society for Me4Teand 1 M (CH2=CH),Te in CsDs were referenced to neat Engineering Education/Office of Naval Technology for R.W.G. Registry No. Me4Te, 123311-08-0;(CH2=CH),Te, 123311(22) Fantoni, R.; Stuke, M. Appl. Phys. B. 1985,38, 209. 09-1; TeCl,, 10026-07-0; MeLi, 917-54-4; (CH2=CH)MgBr, (23) Shriver, D. F.; Drezdzon, M. A. The Manipulations of Air-Sen1826-67-1;129e,14390-73-9;Me2Te, 593-80-6. sitiue Compounds, 2nd ed.; John Wiley & Sons: New York, 1986.
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