摘要:

896 J.C.S. Perkin I1 Verdazyls. Part 30.1 N-I ,N-I '-Linked Biverdazyls (Bis-I ,2,3,4-tetra- hydro-s-tetrazin-I -yls) with a [2.2JParacyclophanylene Bridge By Franz A. Neugebauer and Hans Fischer, Max-Planck-lnstitut fur Medizinische Forschung, Abt. Organische Chemie, Jahnstr. 29, D-6900 Heidelberg, West Germany Three isomeric biverdazyls (3b-d) containing a [2.2]paracyclophanylene bridge have been prepared. The zero- field splitting parameter 10'1could be evaluated from the e.s.r. spectra taken in liquid crystalline solution. The e.s.r. and n.m.r. results of (3b-d), which indicate RT %-IJI %-a,, are discussed with respect to the structure and the distortion about the N-bridge bond. of verdazyls (tetrahydro-s-tetrazin-l-this type.,y4 In these compounds, however, the steric N-1,N-1'-LINKAGE yls) through various conjugated bridges produces dif- interaction between the (CH,),C(NO') substituent and fuse x-electron systems with interesting properties, e.g.the adjacent bridging methylene group causes tlic strong interactions between both unpaired electrons2 nitroxide substituent to be considerably twisted out of Comparable effects might also appear, if there is no conjugation with the phenylene ring.4,5 This is not observed in 3-t-butyl-l-([2.2]paracyclophan-4-y1)-5-10phenylverdazyl, where the arrangement about the [Z.Z]-paracyclophan-4-yl-N-1 bond corresponds to that in 3-t-b~tyl-l,5-diphenylverdazyl.~Furthermore we in--1 tended to carry out a detailed n.m.r. study of [2.2]para- 5/ cyclophanylene-linked biverdazyls, the results of which should reveal further information about transannular 2 interactions in the paracyclophane bridge of such com- a b C pounds.Monosubstitution in each ring of [2.2]paracyclophane leads to the four isomers : pseudo-para (b), pseudo-meta (c), pseudo-ortho (d), and pseudo-geminal (e) . The R -synthesis of the corresponding biverdazyls started out !& from dinitro[2.2]paracyclophanes.6 Catalytic hydro-genation (Pd-BaSO,) yielded the diamino-derivatives R (1b-e). Each isomer exhibits a unique n.m.r. aromatic d e proton pattern (Table 1). In (lb) for the ortho-and pseudo-meta-protons the usual chemical upfield shift is observed (ca. +0.9 p.p.m. relative to the signal for the aromatic protons of [2.2]paracyclophane, 6 6.37) as in the (1) R = NH2 case of aniline or the monoamino-derivative (la).' The distinct downfield shift of the meta and pseudo-geminal protons in (lc) is mainly due to the deshielding effect of the pseudo-geminal amino-substituent .' Most of the direct bond between the two N-phenyl groups of the observed effective shifts (Table l),however, result from verdazyls but the possibility of a transannular inter- superimposed direct substituent and transannular effects.action. The model of choice is the [2.2]paracyclo-Compounds (1b-e) were diazotized and coupled with TABLE1 lH N.m.r. chemical shifts a (6) of amino-substituted [2.2]paracyclophanes pseudo-pseudo-pseudo-pseudo-Compound ortho meta para geminal ortho meta para NH, (la) 723 5.39 6.27 6.08 7.14 -6.35 -6.35 6.58 3.35 (lbj 5.44 6.17 6.59 6.59 6.17 5.44 3.40 6.47 6.95 6.01 6.95 6.01 5.47 3.38(14 ' (Id) 6.16 6.35 6.02 6.16 6.02 6.35 3.35 (14 5.91 6.34 6.07 5.91 6.34 6.07 3.46 Taken on a Bruker WP 80 on dilute solution (ca.1%) in CDCl, with tetramethylsilane as internal standard. phanylene bridge, in which N-phenyl groups of verdazyls 2,Z-dimethylpropanal C2H,]phenylhydrazone to yield the are held face to face at a distance of ca. 3.1 A. Forrester corresponding biformazans (2b-e). 1.r. and n.m.r. and Ramasseul have already synthesized binitroxides of spectra indicate that these bifonnazans, as well as the 897 inonoforinazan (2a) , occupy a trans-syut-form, in which From these e.s.r.spectra only the zero-field splitting intramolecular hydrogen-bonding stabilizes the mole- parameters ID’I can be determined, the parameters IE’I cules in the s-cis-arrangement. When one compares the being apparently too small. Consequently in the first absorption bands of (2b-e) with that of (2a) (Table computer simulations, employing a FORTRAN pro-gram,1° only the parameter ID‘[has been considered. TABLE2 The results of the simulations, including linewidth and Electronic spectral data of formazans (2a-e) and orientational distributions, are summarized in Table 3. verdazyls (3a-d) in dioxan solution; h,,,,./nm (log E) The zero-field splitting parameter 10’1 can be con-Compound verted into a hypothetical average distance Y between (2a) 488 (4.27), 332 (3.62), 273s (3.99), 243sh (4.14) (2b) 495 (4.54), 330sh (3.94), 253 (4.38) (2c) 488 (4.52), 330sh (3.88),240sh (4.40) (2d) 481 (4.51), 345 (3.86), 242sh (4.42) (2e) 457 (4.56), 330sh (3.94), 251 (4.35) (3a) l 664 (3.72), 380sh (3.78), 329 (4.08), 272sh (3.85), 220sh (4.37) (3b) 668 (4.05), 388 (4.09), 328 (4.37), 237sh (4.33) (3c) 664 (4.03), 392 (4.10), 328 (4.36), 273 (4.11), 237 (4.40) (3d) 657 (3.95), 383sh (4.03), 329 (4.36), 276 (4.07), 235sh (4.35) sh = Shoulder.100G2), the pseudo-ovtho-isomer (2d) shows a slight, and the +---~, pseudo-geminal compound (2e) a considerable, hypso- chromic shift. These shifts are obviously caused by steric interactions between the substituents. In (2e) the formazanyl groups are considerably twisted out of conjugation with the phenylene rings of the bridge.The slight bathochromic shift observed for the pseudo-para- isomer (2b) suggests that transannular interactions also contribute to some extent. The biformazans (2b-d) were readily converted into the corresponding biver- dazyls (3b-d) using the usual cyclisation method with Experimental (--) and simulated (----) e.s.r. spectra off~rrnaldehyde.~In case of the biformazan (2e), how- (3d) in nematic phase 5 at 240 K. Signals in the centre of theever, all our attempts failed to obtain the pseudo- spectra (* * --) are due to some monoradical impurity. € is the geminal biverdazyl (3e). angle between the director of the liquid. crystal and the mag- The e.s.r. spectra of the biverdazyls (3b-d) in benzene netic field at room temperature show a broad resonance line the two unpaired electrons using the two point model indicating a poorly resolved hyperfine structure with ID’I = 3gp/4y3.The resulting distances r of the pseudo- a spacing of ca.2.9 G. This is typical for biverdazyls, para-biverdazyl (3b) and the pseudo-ineta-compound (3c) in which the electron exchange parameter J, correspond-agree almost with the distances between the midpoints ing to the energy separation between singlet and triplet of the verdazyl rings (see Table 3, footnote c). For the TABLE3 Compounds (3b-d) in a liquid crystal (nematic phase 5; Merck).a Zero-field splitting parameter ID’/,orientation-dependent linewidth OHB,b parameter A of the orientational distribution function,”J order parameter P,, average distance P between the two unpaired electrons (ID’/ 3gp/4r3), and molecular distance Y’= OHB r-Ap Compound IWG HB/G F/? A p2 4 Y‘lA (3b) 56.2 f0.5 22.0 0 0.5 0.07 7.9 6.4-8.0 (34 68.2 f0.5 22.0 0 -0.3 -0.04 7.4 5.8-7.9 (34 111.8 f0.5 27.0 8.0 1.75 0.26 6.3 4.2-5.2 0 = Angle between the principal axis of the zero-field splitting tensor and magnetic field, E = angle between director of the liquid crystal and magnetic field.OHB = HB + Fsin20. c The molecular distances are estimated from X-ray structure analysis data of 1,3,5-triphenylverdazyl.11 The lowest value in the range given for Y’ is the distance between the bridged N-1,N-1‘ atoms; the highest value represents the distance between the midpoints of the verdazyl rings.states, is considerably larger than the nitrogen splitting pseudo-ortho-biverdazyl (3d), however, the calculated of ca. 5.9 G (IJI & a~).~The line broadening is caused distance r suggests that the average centres of the un- by the strong magnetic dipolar interaction of both un- paired electrons are slightly shifted beyond the verdazyl paired electrons. The triplet state of (3b-d) is clearly midpoints, apparently a consequence of the steric confirmed by the e.s.r. spectra taken in liquid crystalline arrangement in (3d). Due to the pseudo-ortho-sub-solutions (nematic phase 5; Merck) at 240 K (Figure). stitution the verdazyl rings in (3d) are twisted out of conjugation with the phenylene rings of the bridge to a large extent.This increased distortion about the N- bridge bond in (3d) is also indicated by the hypso chromic shift of the first absorption band, when one compares the data of the electronic spectra of (3a-d) in Table 1. N.m.r. paramagnetic shifts (all)of organic free radicals render directly the sign and the magnitude of electron- nuclei coupling constants (ai).l29l3 Based on the Reitz- Weissman model l4>l5of the electronic structure of bi- radicals, 6,) is related to ai by equation (1).16 In 6p = -Hp)/Hd = aigPye/k;Tyi[3+ exp(J/RT)J (1) biradicals satisfying IJI < RT equation (1) is reduced to (2) which can be written a, = Ci(T)6p; CH (300 K) = 1.35 x G/p.p.m., Cu (300K) = 2.08 x G/p.p.m. ap = aigPye/4kTyi (2) Equation (2) is in accord with the corresponding equation for monoradicals.Therefore the same paramagnetic shifts are expected for corresponding protons in biver- dazyls satisfying IJI RT and in structurally related monoverdaz yls. The n.m.r. spectra of (3b-d) in di-t-butyl nitroxide l7 are sufficiently resolved and were analysed by compari- son of the individual spectra and by analogy with the n.m.r. results of (3a).l The data obtained are listed in Table 4. Comparing the n.m.r. results of (3b-d) with those of (3a),l excellent agreement is found for ac;((jF18)8-H= 0.11 (&o.ol), &*,6'-1> = -0.160 (&0.003), a3',5'-~ 0.060 (&-O.OOl), and a4~~= -0.172 (k0.002) G. These results clearly show that the biverdazyls (3b-d) satisfy RT 9 IJI 9 UN.Excellent agreement is also found for the aromatic bridge proton splittings of (3b and c) com- pared with the corresponding values of (3a) : a5,1sF1(3b) w a5,1~~(3c)w a5-~(3a)= -1.02 (h0.03) G, a8,16-~(3b) x as,15-~(3c)w as-lx(3a)= 0.56 (&0.02) G, and qJ5-11- (3b) w U,,16-~(3C) G a743a) = -1.03 (hO.01)G. These data represent splittings of protons, which are directly connected with carbons bearing spin density (a to pc). According to these splittings the varied bridging in (3a-c) apparently does not affect the spin density distribution in the phenylene rings of the bridge. The splittings a2,10-~(3b)w UI,~-H(~C)z &-&$a)= 0.77 (k0.06) or 0.20 (h0.02) G stem from protons P to pu [aH = (B, + Bcos20)pU].Here the small deviations beyond the experimental error (53%)may be connected, at least in part, with slight changes in the spatial arrange- ment (cos 0) of the [2.2]paracyclophanylene bridge caused by different verdazyl substitution. In (3d), however, the splittings of the [2,2]paracyclophanylene protons differ from those hitherto discussed. Ob-viously, due to the steric requirements of pseudo-ortho- substitution the verdazyl rings are twisted out of con-jugation with the [2.2]paracyclophanylene bridge to a large extent [also indicated by 10'1 of (3d) and its ab- sorption spectrum]. Consequently the spin density J.C.S. Perkin I1 delocalisation into the phenylene rings of the bridge is reduced leading to smaller splittings of the aromatic protons.Additionally a distinct increase in one ortho-inethylene proton splitting (a2,10-~~ 0.96 G) is observed. This increase of P-proton splitting with rising distor- tion angle about the N-bridge bond is apparently con- nected with an increasing long-range interaction. In particular homohyperconjugation 18,19of the methylene proton anti to the verdazyl substituent would gain most from rising distortion about the N--bridge bond. There-fore we attribute the larger positive methylene proton TABLE4 H and D paramagnetic shifts 6, = (Hd -Hp)/Hdaand coupling constants UH and ar) of (3b-d) in di-t-butyl nitroxide at 300 K 5' Compound Assignment 6, (p.p.m.) UD/G aH/G (3b) 1,1,9,9-H4 2,lO-HZ 52.7 0.71 2, 10-H2 16.3 0.22 5,13-H, -73.4 -0.99 7,15-H, -77.0 -1.04 8,16-H, 43.0 0.68 [C(CH3)312-H18 8.2 0.11 (2',6') 2-1>4 -78.5 -0.163 -1.06 (3',5')2-D4 28.9 0.060 0.39 4'2-D~ -83.7 -0.174 -1.13 (3C) 1,2-H2 60.9 0.82 1,2-H, 14.0 0.19 5,7, 1%,16-H4 -75.8 -1.02 8,15-H2 41.1 0.55 9,10-H2 -8.4 -0.11 9,lO-HS 8.2 0.11 -77.4 -0.161 -1.04 28.7 0.060 0.39 -82.4 -0.171 -1.11 -7.9 -0.11 -4.3 -0.06 71.4 0.96 13.5 0.18 -55.9 -0.76 -67.7 -0.91 37.3 0.50 8.9 0.12 -75.8 -0.158 -1.02 28.5 0.059 0.38 -83.3 -0.173 -1.12 Shift relative to the corresponding H or D resonance in the parent [2.2]paracyclophane derivative (2b-d).Partly cal- culated from uD; uH = 6.61aD. These resonances could not be resolved or definitely assigned.Measured in CDCl,. Tentatively assigned, may be in reverse order. splitting (UH 0.96 G) to the a~zti-2,10-protons, for which spin polarisation, hyperconjugation, and homohyper- conjugation reinforce each other. Not only the n.m.r. results but also the 10'1values of (3b-d) reveal no indication of a substantial trans-annular interact iofi within the [2.2]paracyclophanylene bridge of these compounds. Unfortunately we did not succeed in synthesizing the pseudo-geminal biverdazyl (3e), which would have been a neat example of a biver-dazyl with an almost fixed molecular structure. EXPERIMENTAL N.M.R. of Compounds (3b-d) .-The paramagnetic shifts were measured as described for (3a).l The n.m.r. spectra of the diamagnetic compounds were taken on a Bruker WP 80 spectrometer, the absorption spectra on a Cary 17 instru-ment.4,12-Dinmino[2.2]paracycZophane (1 b) .-4,12-Dinitro- [2.2]paracyclophane (3.0 g) in dioxan (80 ml) was hydro- genated (6 mol. equiv. H,) in the presence of 10% Pd- BaSO, (1.0g). After separation of the catalyst water was added to the filtrate to precipitate the product. Crystal-lisation from methanol yielded crystals (1.6 g, 67y0), m.p. 288-289" (lit.,' 267-268") (Found: C, 80.8; H, 7.85; N, 11.55. Calc. for C16Hl,N,: C, 80.65; H, 7.6; N, 11.75%). 4,12-Bis(acetamido)[Z.2]paracycZo~hnne.-A solution of (lb) (30 mg) in acetic anhydride (0.5 ml) was heated to the b.p. Crystals from acetic acid had m.p. 356-357" (Found: C, 74.75; H, 6.9; N, 8.8.C,,H,,N,O, requires C, 74.55 H, 6.9; N, 8.7%). 4,13-Diamino[2.2]paracycZo~hane (lc).-4.13-Dinitro-[2.2]paracyclophane (3.O g) was hydrogenated as described for (lb), yielding crystals (2.1 g, 88y0)from methanol, m.p. 256-257" (lit.,' 222-226") (Found: C, 80.75; H, 7.45; N, 1 1.85 yo).4,13-Bis(acetamido)[2.2]paracycZophane.-Acetylation of (lc) as described above gave crystals, m.p. 354-355" (Found: C, 74.65; H, 6.55; N, 8.95%). 4,16-0iamino[2.2]paracycZophane (Id) .-4,16-Dinitro- [2.2]paracyclophane (3.0 g) was hydrogenated as described for (lb) to yield crystaZs (2.0 g, 84%) from methanol, m.p. 263-264" (Found: C, 80.35; H, 7.9; N, 11.8yo). 4,16-Bis(acetamido)[2.2]paracycZophane.-Acetylation of (Id) as described above yielded crystals, m.p.317-318" (Found: C, 74.45; H, 7.05; N, 8.95%). 4,15-Diamino[2.2]para;cyclophune (le) .-4,15-Dinitro- [2,2]paracyclophane 6 (1.5 g), 10% Pd-BaSO, (500 mg), and dioxan (40 ml) were treated as described for (lb). Brownish crystals (850 mg, 71%) from methanol-water had m.p. 245-247" (Found: C, 80.45; H, 7.85; N, 11.87%). 4,15-Bis(acetamido)[2.2]pavacyclophane.-Acetylation of (le) as described above gave crystals, m.p. 245-247" (Found: C, 74.65; H, 6.95; N, 8.75%). 4,12-Bis-(3-t-b~tyZ-5-[~H,]phenyi&ormazan-1 -yl) [2. 2]para- cydophane (2b).-The mixture of (lb) (1.5g) in dimethyl- formamide (30 ml) and concentrated HC1 (5ml) was cooled to 0" and kept at this temperature while the solution of NaNO, (900 mg) in H,O (10 ml) was added dropwise under stirring.This diazonium salt solution was added in small portions to the stirred mixture of 2,2-dimethylpropanal [2H,]phenylhydrazone (3.0 g) and sodium acetate (15 g) in dimethylformamide (40 ml) and methanol (15 ml) kept at -10". Stirring was continued for 1 h. After addition of water (100 ml) the precipitated yellow azo-compound was collected, dissolved in dimethylformamide (50 ml), and re- arranged by addition of methanolic KOH (saturated; 1 ml). After 15 min the biformazan was precipitated by addition of methanol and filtered. Crystallisation from dioxan-ethyl acetate-methanol yielded brown crystals (1.9 g, 48%), m.p. 203-204" (decomp.),6 ([2H,]DMSO; 80 MHz) 1.48 [18 H, s, C(CH,),], 2.8-4.0 (8 H, m, CH,), 6.0-7.0 6 H, m, aromatic H), and 14.15 (2 H, s, NH) (Found: C, 73.3; H + D, 8.9; N, 17.95.C,,H,,D,,N, requires C, 73.25; H + D, 8.75; N, 18.0%). 4,13-Bis-(3-t-butyl-5-[2H,lphenyZfo~mazun-l-yZ)[2.2]para-cyclophane (2c).-This was prepared from (lc) (1.5 g) as described above. Red-brown crystals (2.3 g, 59%) from dioxan-ethyl acetate-methanol, m.p. 181-182" (decomp.) 6 ([2Hg]DMSO; 80 MHz) 1.48 [18 H, s, C(CH,),], 2.8-4.0 (8 H, m, CH,), 6.42 (2 H, s, aromatic H), 6.83 (2 H, s, aromatic H), 8.01 (2 H, s, aromatic H), and 14.0 (2 H, s, NH) (Found: C, 73.15; H + D, 9.15; N, 17.8%). 4,16-Bis-(3-t-butyl-5-[2H,]fihenyZformazan-l-yZ) [2.2]para- cyclophane (2d).-This was prepared from (Id) (1.5 g) as described above. After the rearrangement the reaction mixture was partitioned between water and diethyl ether, the organic phase washed three times with water, dried (MgSO,), and the solvent evaporated.The residue was purified by chromatography on A1,0, (Brockmann), using cyclohexane as eluant, to yield red-brown crystals (1.3 g, 33%) from ethyl acetate-ethanol (1 : 2), m.p. 147-149" (decomp.),6 ([2H6]DMSO; 80 MHz) 1.25 [18 H, s, C(CH,),], 2.8-4.0 (8 H, m, CH,), 6.62 (2 H, s, aromatic H), 6.84 (4 H, s, aromatic H), and 13.41 (s, 2 H, NH) (Found: C, 73.45; H + D, 8.85; N, 17.85%). 4,15-Bis-(3-t-butyl-5-[2H,]phenyZformuzan-1-yl) [2. 21para- cyclophane (2e).-Compound (le) (600 mg) was treated as described for (2b) to yield red-brown crystals (600 mg, 38%) from ethyl acetate-ethanol(1 : 2), m.p.195-196" (decomp.), 6 ([2H6]DMSO; 80 MHz) 1.23 [18 H, S, C(CH,),), 2.8-4.0 (8 H, m, CH,), 6.76 (4 H, s, aromatic H), 6.83 (2 H, s, aro-matic H), and 13.95 (2 H, s, NH) (Found: C, 73.35; H + D, 8.7; N, 17.9%). 4,12-Bis- (3-t-butyl-5- [2H,]phenylverdazyl- 1-yl) [2. 2lpara-cyclophane (3b) .-Compound (2b) (1.5 g), KHSO, (2 g), and paraformaldehyde (500 mg) in dimethylformamide (70 ml) were stirred for 30 h. After filtration the solution was cooled to 0" and 40% aqueous formaldehyde (5 ml) added. Then ~N-N~OHwas added dropwise to the stirred solution until the violet colour changed to green. The mixture was partitioned between benzene and water, the benzene layer washed three times with water, dried (MgSO,), and the solvent evaporated.The residue was purified by chromato- graphy on A1,0, (Brockmann), using benzene as eluant, to yield black crystals (800 mg, 51%) from benzene-ligroin, m.p. 206-207" (decomp.), microhydrogenation, (3b) (4.85 mg) + 5% Pd-BaSO, (20 mg) in dimethylformamide (2 ml) ; 1.04 mol H, after 60 min (end value) (Found: C, 74.25; H + D, 9.1; N, 17.2. C4,H3,D10N8 requires C, 74.05; H + D, 8.7; N, 17.25%). 4,13-Bi~-(3-t-butyl-5-[~H,]Phenylverdaxyl-l-yl)[2.2]para-cyclophane (3c).-Compound (2c) (1.5 g) was treated as described above for (3b), giving black crystals (750 mg, 48%) from benzene-ligroin, m.p. 198-199" (decomp.), microhydrogenation, (3c) (7.21 mg) + 5% Pd-BaSO, (20 mg) in dimethylformamide (2 ml); 1.00 mol H, after 60 min (end value) (Found: C, 73.75; H + D, 8.95; N, 17.25yo).4,16-Bis-(3-t-butyl-5-[2H,]Phenyluerduzyl-1-yl) [2.2]para- cyclophane (3d).-This was prepared from (2d) (1.2 g) as described for (3b). The residue was chromatographed on A1,0, (Brockmann), using cyclohexane-benzene (4 : 1) as eluant, to yield black crystaZs (600 mg, 48%) from cyclo- hexane-ligroin, m.p. 181-182" (decomp.), microhydro- genation (3d) (8.96 mg) + 5% Pd-BaSO, (20 mg) in di- methylformamide (2 ml); 0.99 moles H, after 60 min (end value) (Found: C, 74.2; H + D, 8.8, N, 17.25%). We thank Dr. G. Kothe for help in the interpretation of the triplet e.s.r. spectra and Dr. H. Brunner for the Bruker Spectrospin HX-90 MHz n.m.r. measurements. [0/1692 Received, 6th November, 19801 REFERENCES Part 29; F.A. Ncugebauer, H. Fischcr and H. Brunner, Tetrahedron, in the press. a F. A. Neugebauer, R. Bernhardt and H. Fischer, Chem. BBY., 1977, 110, 2254. A. R. Forrester and R. Ramasseul, J. Chem. SOC.B, 1971, 1638. A. R. Forrester and R. Ramasseul, J. Chem. SOC.B, 1971, 1645. A. R. Forrester and R. Ramasseul, J. Chem. SOC.,Perkin Trans. 1, 1975, 1753. H. J. Reich and D. J. Cram, J. Am. Chem. SOC.,1969, 91, 3527. H. Allgeier, M. G. Siegel, R. C. Helgeson, E. Schmidt, and D. J. Cram, J,Am. Chem. SOC.,1975, 97, 3782. J.C.S. Perkin I1 D. J. Cram and N. L. Allingcr, J. Am. CImi. SOC.,1956, 77, 6289. R. Kuhn and H. Trischmann, Monatsh. Chem., 1964,95, 457. lo E. Ohmes and G. Kothe, unpublished results. l1 D. E. Williams, J. Am. Chem. SOL, 1969, 91, 1243. l2 E. de Boer and C. MacLean, Mol. 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ISSN:1472-779X    

DOI:10.1039/P29810000896

出版商:RSC    

年代:1981

数据来源: RSC