寄稿論文 酸を用いない芳香族化合物の新しいニトロ化法 | 東京化成工業
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- けいざぶろう さどひら
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1 Table 1. A List of Known itrating Agents itric acid Alone or in combination with H 2 S 4, H 3 P 4, H 4, HF(BF 3 ), CF 3 C 2 H, S 3 H, CF 3 S 3 H, FS 3 H(SbF 5 ), sulfonated resins, clays, molecular sieves, graphite itrate salts Ag 3 /BF 3, K 3 /Al 3, Cu( 3 ) 2 /(C) 2, H 4 3 /(CF 3 C) 2, (H 4 ) 2 Ce( 3 ) 6 itrate esters Bu /afion-h, /BF 3, 3 Si, acetone cyanohydrin nitrate itryl compounds BF 4, PF 6, 4, (F), C 2, CF 3 C 2, PhC 2, -nitropyridinium nitrate itrogen oxides 2 3 /BF 3, 2 4 /H 2 S 4, 2 4 /Al 3, 2 5 itroalkanes C( ) 4, CH( ) 3, ( 2 ) 3 CC( ) 3 2
2 2 H KJ/mol X (Scheme 1) (Scheme 1)
3 (Scheme 2) δ δ δ 3 δ δ 3 δ 3 3 (Scheme 2) 2 (Scheme 3) H H H 2 2 H 4 H H 3 (Scheme 3) Pb( 3 ) 2 4
4 (kyodai-nitration) BF 3 Et BF 3 Et 2 Scheme 4 5
5 Table 2. The Kyodai-itration of Substituted Benzenes a - 3 CH 2 2, 0 C substrate 1 yield isomer distribution (%) o:p (o:m) = (%) ratio Et i Pr t Bu F ~ 14 0 ~ 1 86 ~ ~ ~ 53 0 ~ 3 47 ~ ~ 1.14 Br ~ 51 3 ~ 4 46 ~ ~ 1.09 C (1.1) t BuC (3.8) C 2 H (0.38) C 2 88 b (0.47) C (0.01) CEt 2 72 b (1.0) CF c (0.01) C 93 b (0.31) (0.09) HC d C (CH 2 ) CH 2 C a eactions were carried out in dichloromethane at 10 ~ 0, unless otherwise indicated. b 1,2-Dichloroethane was used as the solvent. c thanesulfonic acid was added as a catalyst. d Chloroform was used as the solvent C 3 C fum-h 3 -fum-h 2 S 4, % - 3, H (cat.), hexane, -10 >95% (Scheme 4) 7 fum-h 3 -fum-h 2 S 4, % - 3, H (cat.), CH 2 2, 0 97% 6
6 - 3 CH 2 2, 0 C (Scheme 5) H 3 -H 2 S 4, 1-/2- = 7.7 ~ 11-3, CH 2 2, 0 1-/2- = 12 ~ 16 (Scheme 5) Table 3. Comparison of the atios of the Most Abundant Isomer to the Sum of All ther Isomers Formed in the itration of aphthalenes substrate a conditions of nitration a ArH a - 3 naphthalene 10 ~ ~ ~ 70 1-methylnaphthalene ~ 13 2-methylnaphthalene ~ 4.0 a From reference 13. 7
7 Figure 1. Time course of the progressive kyodai-nitration of hydrocarbon 5 to musk xylol 6. The reaction was carried out at -10 in hexane. Hydrocarbon 5 Dinitro derivatives Mononitro derivatives Musk xylol Figure 2. Dependence of the ortho-para isomer distributions on the initial concentration of chlorobenzene. Mg (Scheme 6) ( CH() 2 ) ( C() 3 ) 8
8 log [Ph /M] - 3, Mg CH 2 2, 0 C = Et t Bu ortho:meta:para yield (%) 22 : 19 : : 25 : (Scheme 6) CH(Ac) CH(Ac) 2 CH 2 2, 0 C ortho:meta:para 55 : 28 : 17 Scheme 7 (Scheme 8) C Kyodai-nitration - 3 Conventional nitration H 3 -H 2 S 4 Protection as acetal Kyodai-nitration ( - 3 ) Deprotection C C C C 2 M C 2 Η CH 2 2, 0 C M = Li K 1/2 Ca 1/2 Cu ortho:meta:para 21 : 78 : 1 26 : 73 : 1 9 : 89 : 2 30 : 68 : 2 (Scheme 7) (Scheme 8) 9
9 Scheme 9 (o : p = 3.3) (2,4- : 2,6- = 2.2 ~ 2.5) HC 13 = CH 2 2, 0 C i Pr C ortho:meta:para yield (%) 81 : 0 : : 0 : : 0 : HC (Scheme 9) (o: p = 1.2 ~ 1.5) (Scheme 10) Scheme (CH 2 ) n - 3 CH 2 2, 0 C n = 2 (CH 2 ) n ortho:meta:para yield (%) 1 69 : 4 : 27 > : 3 : 26 > : 3 : 59 >90 (Scheme 10) CH 2 C 2 2 CH 2 C 2 ortho:meta:para yield (%) 19 : 29 : : 4 :
10 C 2 Bakke 2 5 ahs 3 (Scheme 11) S 3 a - 3 ahs 3 CH 2 2, 0 C H (Scheme 11) C (Scheme 12) C (Scheme 13) 11
11 H 17-3 CH 2 2, 0 C H 3 -H 2 S H 2 3 CH 2 2, 0 C (Scheme 12) 19 H 3 S 3 H CH 2 2, 0 C 2 H 3 (S 3 H) CH 2 2, 0 C C 2 Et 3 C 23-3 M (cat.) C 2 H 4 2, 5 C - 3 M (cat.) C 2 H 4 2, 5 C 2 3 C C 2 Et (Scheme 13) C C C (Scheme 14) C (Scheme 14) CH2 2 H, 0 C 29 12
12 3 3 C C 2 2 (Scheme 15) (Scheme 15) 2 ArH 2 3 Ar H 3 2 (1) Hammett Brown σ r = ρ =
13 Figure 3. Hammett plot from the competitive kyodai-nitration. 3 (Z 0 = 2.3~2.6 V vs HE) (2) ArH ArH 3 3 (3) ArH H Ar(H) Ar (4) H H3 (5) H ArH Ar(H) Ar (6) 3 (Scheme 16) - 3 CH 2 2, 20 C CH 2 H 33 2 BF 4 69% 17% 14% no ring nitration (Scheme 16) CH 2 2, 0 C 100% (o : m : p = 8 : 24 : 68) no fragmentation 14
14 Table 4. Unusual ta rientation bserved at the Initial Stage of the KyodaiÐitration substrate Py a t b conv. c isomer proportion (%) (equiv) (min) (%) ortho : meta : para toluene : 77 : 8 chlorobenzene : 91 : 2 chlorobenzene : 71 : 20 chlorobenzene : 46 : 33 anisole : 54 : 21 a Pyridine. b eaction time. c Conversion. Scheme H H (Scheme 17) H H 3 H H Scheme Scheme 19 15
15 CH(D) 2 CH(D) 2 CD 3 34 CD(H) 3 35 H(D) CD(H) 3 36 H(D) (Scheme 18) Intramolecular 35 H /35 D 36 H /36 D kinetic isotope effect Ac X v H /v D ~6 HX v H /v D ~1.5 v H /v D = k H /k D ~6 k H /k D ~5 k H /k D =1 k H /k D =1 H CH 2 H (Scheme 19) H H CH 2 CH 2 40 CH 2 CH 2 CH CH 2 16
16 (Scheme 20) 2 2 (Scheme 20) ) Industrial Commodity Statistics Yearbook 1995, United ations, ew York, ) Mitscherich, E. Annln. Phys. Chem. 1834, 31, ) (a) Albright, L.F.; Carr..V.C.; Schmitt,.J. Eds. itration; ACS Symposium Series 623, (b) Schofield, K. Aromatic itration; Cambridge University Press: London, (c) lah, G.A.; Malhotra,.; arang, S.C. itration: thods and chanisms; VCH Publishers Inc.: ew York,
17 4) Suzuki, H.; Murashima, T.; Shimizu, K.; Tsukamoto, K. Chem. Lett. 1991, ) (a) Matsunaga, M. Chimica ggi 1994, (b) Suzuki, T.; oyori,. Chemtracts. 1997, 10, (c) Mori, T.; Suzuki, H. Synlett 1995, (d) idd, J. H. Acta Chem. Scand. 1998, 52, 11. (e) onoyama, ; Mori, T.; Suzuki, H. Zh. rg. Khim. 1998, 34, ) Suzuki, H.; Murashima, T.; Kozai, I.; Mori, T. J. Chem. Soc., Perkin Trans , ) Suzuki, H.; Murashima, T.; Shimizu, K.; Tsukamoto, K. J. Chem. Soc., Chem. Commun. 1991, ) Suzuki, H.; Mori, T. J. Chem. Soc., Perkin Trans , ) Suzuki, H.; Mori, T. J. Chem. Soc., Perkin Trans , ) (a) Bauer, A. Chem. Ber. 1891, 24, (b) Suzuki, H.; Hisatome, K.; onoyama,. Synthesis, 1999, ) Jackson, T.G.; orris, J.E.; Legendre,.C. J. rg. Chem. 1971, 36, ) Suzuki, H.; Mori, T. J. Chem. Soc., Perkin Trans , ) Eberson, L.; Hartshorn, M.P.; adner, F. Acta Chem. Scand. 1994, 48, ) Suzuki, H.; Murashima, T.; Shimizu, K.; Tsukamoto, K. Chem. Ind. (London) 1991, ) Suzuki, H.; Mori, T.; Maeda, K. J. Chem. Soc.,Chem. Commun. 1993, ) Suzuki, H.; Mori, T. J. Chem. Soc., Perkin Trans , ) Suzuki, H.; Mori, T.; Maeda, K. Synthesis 1994, ) Suzuki, H.; Yonezawa, S.; Mori, T.; Maeda, K. J. Chem. Soc., Perkin Trans , ) Suzuki, H.; Yonezawa, S.; Mori, T. Bull. Chem. Soc. Jpn. 1995, 68, ) Suzuki, H.; Tomaru, J.; Murashima, T. J. Chem. Soc., Perkin Trans , ) Suzuki, H.; onoyama,.; Tomaru, J.; Mori, T. Zh. rg. Khim., 1996, 32, ) Suzuki, H.; Tatsumi, A.; Suzuki, H.; Maeda, K. Synthesis 1995, ) Suzuki, H.; Ishibashi, T.; Marashima, T.; Tsukamoto, K. Tetrahedron Lett. 1991, 32, ) Suzuki, H.; Tatsumi, A.; Ishibashi, T.; Mori, T. J. Chem. Soc., Perkin Trans , ) Hartshorn, S..; Moodie,.B.; Shofield, K. J. Chem. Soc. B 1971, ) Suzuki, H.; Takeuchi, T.; Mori, T. J. rg. Chem. 1996, 61, ) Strazzolini, P.; Verardo, G.; Gorassini, F.; Giumanini, A.G. Bull. Chem. Soc. Jpn. 1995, 68, ) Suzuki, H.; Murashima, T.; Tatsumi, A.; Kozai, I. Chem. Lett. 1993, ) Suzuki, H.; Murashima, T. J. Chem. Soc., Perkin Trans , ) Barker, S.D.; orris,.k.; andles, D. Aust. J. Chem. 1981, 34, ) Suzuki, H.; Kozai, I.; Murashima, T. J. Chem. es. (S) 1993, ) Bakke, J.M.; Hegbom, I.; vreeide, E.; Aaby, K. Acta Chem. Scand. 1994, 48, ) Bakke, J.M.; anes, E. Synthesis 1997, ) Suzuki, H.; Iwaya, M.; Mori, T. Tetrahedron Lett. 1997, 38, ) Suzuki, H.; onoyama,. J. Chem. es. (S) 1996, ) Suzuki, H.; Suzuki, H.; to be published. 37) Suzuki, H.; onoyama,. J. Chem. Soc., Chem. Commun. 1996, ) Suzuki, H.; onoyama,. J. Chem. Soc., Perkin Trans , ) Suzuki, H.; Mori, T. J. rg. Chem. 1997, 62, ) Suzuki, H.; Takeuchi, T.; Mori, T. Bull. Chem. Soc. Jpn. 1997, 70, ) Suzuki, H.; Mori, T. Chem. Lett., 1996, ) Suzuki, H.; Mori, J. Chem. Soc., Perkin Trans , ) Suzuki, H.; Murashima, T.; Mori, T. J. Chem. Soc., Chem. Commun. 1994, ) Suzuki, H.; Mori, T. J. Chem. Soc., Perkin Trans , ) Suzuki, H Synthesis 1977, ) onoyama,.; Iwaya, M.; Suzuki, H. Tetrahedron Lett. 2000, 41, ) Tokiwa, H.; hnishi, Y. CC Crit. ev. Toxicol. 1986, 17, 23-60; World Health Statistics Annual, WH, Geneva, ) Enya, T.; Suzuki, H.; Watanabe, T.; Hirayama, T.; Hisamatsu, Y. Environ. Sci. Technol. 1997, 31, ) Kawanishi, M.; Enya, T.; Suzuki, H.; Takebe, H.; Matsui, S.; Yagi, T. Chem. es. Toxicol. 1998, 11, ) Enya, T.; Suzuki, H.; Hisamatsu, Y. Bull. Chem. Soc. Jpn. 1998, 71,
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1 a C CF b c 4 5 Me Me S Jacobsen's catalyst Scheme 1. eagents and conditions: (a) C (1.5 equiv), Jacobsen's catalyst (0.05 equiv), toluene, 0 C, 40 h, then trifluoroacetic anhydride (4.0 equiv), 60 C,
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