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Volumn 61, Issue 6, 1996, Pages 2085-2094

Selective 1,4-addition of arenes to 3-chloro-3-cyclobutene-1,2-dione under friedel-crafts conditions. Synthesis and reactivity of 4-aryl-3-chloro-2- hydroxy-2-cyclobuten-1-ones

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALUMINUM CHLORIDE; AROMATIC COMPOUNDS; ETHERS; MIXTURES;

EID: 0012180469     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952062r     Document Type: Article
Times cited : (11)

References (68)
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    • Oxocarbons and Related Compounds; Part 23. Part 22: Schmidt, A. H.; Kircher, G.; Künz, Ch.; Wahl, S.; Hendriok, M. W. J. Org. Chem. 1995, 60, 3890.
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    • For publications dealing completely or in part with the reaction of squaric dichloride with aromatics and offering full to almost no experimental details, see: (a) Maahs, G, Hegenberg, P. Angew. Chem. 1966, 78, 927;
    • For publications dealing completely or in part with the reaction of squaric dichloride with aromatics and offering full to almost no experimental details, see: (a) Maahs, G.; Hegenberg, P. Angew. Chem. 1966, 78, 927;
  • 11
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    • 3 (3 equiv). Yield 33%; mp 190-191 °C.
    • 3 (3 equiv). Yield 33%; mp 190-191 °C.
  • 12
    • 76049130050 scopus 로고    scopus 로고
    • Akasaki, Y, Tokida, A, Torigoe, K, Imai, A. Japanese Patent 62,249,952; 30 Oct 1987; Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1988, 109, 170005s. Described here is the preparation and characterization of fourteen 3-[4-(N,N-dialkylamino)-phenyl]-4- chlorocyclobutenediones. The reaction between squaric dichloride (1) and the N,N-dialkylaniline is carried out in the presence of BF3-etherate. However, the reaction proceeded more satisfactorily without a catalyst. Thus, the desired compound is obtained in higher purity than the product obtained in the presence of a Lewis acid catalyst
    • (j) Akasaki, Y.; Tokida, A.; Torigoe, K.; Imai, A. Japanese Patent 62,249,952; 30 Oct 1987; Fuji Xerox Co., Ltd., Japan; Chem. Abstr. 1988, 109, 170005s. Described here is the preparation and characterization of fourteen 3-[4-(N,N-dialkylamino)-phenyl]-4- chlorocyclobutenediones. The reaction between squaric dichloride (1) and the N,N-dialkylaniline is carried out in the presence of BF3-etherate. However, the reaction proceeded more satisfactorily without a catalyst. Thus, the desired compound is obtained in higher purity than the product obtained in the presence of a Lewis acid catalyst.
  • 13
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    • Japanese Patent 62,249,953; 30 Oct, Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1988, 109, 170004r
    • (k) Akasaki, Y.; Tokida, A.; Saeki, S.; Torigoe, K.; Imai, A. Japanese Patent 62,249,953; 30 Oct 1987; Fuji Xerox Co., Ltd., Japan; Chem. Abstr. 1988, 109, 170004r.
    • (1987)
    • Akasaki, Y.1    Tokida, A.2    Saeki, S.3    Torigoe, K.4    Imai, A.5
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    • Japanese Patent 01,146,865; 8 June, Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1989, 111, 232571a
    • (l) Akasaki, Y.; Tokida, A.; Torigoe, K.; Imai, A. Japanese Patent 01,146,865; 8 June 1989; Fuji Xerox Co., Ltd., Japan; Chem. Abstr. 1989, 111, 232571a.
    • (1989)
    • Akasaki, Y.1    Tokida, A.2    Torigoe, K.3    Imai, A.4
  • 17
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    • The results reported in the literature on the reaction of squaric dichloride (1) with benzene (2a) are partly contradictory: See refs 2a and 2c. Furthermore, we were not able to establish one of the published procedures as a general one for the generation of 3-aryl-4- chlorocyclobutenediones 12: Schmidt, A. H.; unpublished results. See also ref 2n.
    • The results reported in the literature on the reaction of squaric dichloride (1) with benzene (2a) are partly contradictory: See refs 2a and 2c. Furthermore, we were not able to establish one of the published procedures as a general one for the generation of 3-aryl-4- chlorocyclobutenediones 12: Schmidt, A. H.; unpublished results. See also ref 2n.
  • 18
    • 76049099427 scopus 로고    scopus 로고
    • In extension of the patent cited in ref 2j, several recent patents and papers describe the preparation of a large number of new 3-[4-(N,N-dialkylamino)phenyl]-4-chloro-3-cyclobutene-1,2-diones as well as structurally related compounds. For selected references, see: (a) Nakazumi, H. Japanese Patent 06,184,109; 5 July 1994; Mitsubishi Chem. Ind, Japan. Chem. Abstr. 1995, 122, 132976v
    • In extension of the patent cited in ref 2j, several recent patents and papers describe the preparation of a large number of new 3-[4-(N,N-dialkylamino)phenyl]-4-chloro-3-cyclobutene-1,2-diones as well as structurally related compounds. For selected references, see: (a) Nakazumi, H. Japanese Patent 06,184,109; 5 July 1994; Mitsubishi Chem. Ind., Japan. Chem. Abstr. 1995, 122, 132976v.
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    • Japanese Patent 06,184,134; 5 July, Mitsubishi Chem. Ind, Japan. Chem. Abstr. 1995, 122, 105672m
    • (b) Nakazumi, H. Japanese Patent 06,184,134; 5 July 1994; Mitsubishi Chem. Ind., Japan. Chem. Abstr. 1995, 122, 105672m.
    • (1994)
    • Nakazumi, H.1
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    • Japanese Patent 06,100,511; 12. April 1994; Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1994, 121, 121397k
    • (c) Nishikata, Y.; Tomono, T.; Fu, R. Japanese Patent 06,100,511; 12. April 1994; Fuji Xerox Co., Ltd., Japan; Chem. Abstr. 1994, 121, 121397k.
    • Nishikata, Y.1    Tomono, T.2    Fu, R.3
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    • Japanese Patent 04,202,166; 22. July 1992; Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1992, 117, 261281k
    • (f) Fu, R. Japanese Patent 04,202,166; 22. July 1992; Fuji Xerox Co., Ltd., Japan; Chem. Abstr. 1992, 117, 261281k.
    • Fu, R.1
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    • Japanese Patent 04,202,165; 22 July, Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1992, 117, 261280j
    • (g) Fu, R. Japanese Patent 04,202,165; 22 July 1992; Fuji Xerox Co., Ltd., Japan; Chem. Abstr. 1992, 117, 261280j.
    • (1992)
    • Fu, R.1
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    • Japanese Patent 01,146,848; 8 June, Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1989, 111, 232276h
    • (h) Akasaki, Y.; Tokida, A.; Torigoe, K.; Imai, A. Japanese Patent 01,146,848; 8 June. 1989; Fuji Xerox Co., Ltd., Japan; Chem. Abstr. 1989, 111, 232276h.
    • (1989)
    • Akasaki, Y.1    Tokida, A.2    Torigoe, K.3    Imai, A.4
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    • Japanese Patent 62,249,951; 30 Oct, Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1988, 109, 210668u
    • (i) Akasaki, Y.; Torigoe, K.; Imai, A.; Tokida, A.; Saeki, S. Japanese Patent 62,249,951; 30 Oct 1987; Fuji Xerox Co., Ltd., Japan; Chem. Abstr. 1988, 109, 210668u.
    • (1987)
    • Akasaki, Y.1    Torigoe, K.2    Imai, A.3    Tokida, A.4    Saeki, S.5
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    • Ried, W.; Schäfer, D. P. Chem. Ber. 1969, 102, 4193. Presented here are also mechanistic details on the reactions of 3-chloro-4-phenylcyclobutene-1,2-dione and 3-phenylcyclobutene-1,2-dione with arenes under Friedel-Crafts conditions.
    • Ried, W.; Schäfer, D. P. Chem. Ber. 1969, 102, 4193. Presented here are also mechanistic details on the reactions of 3-chloro-4-phenylcyclobutene-1,2-dione and 3-phenylcyclobutene-1,2-dione with arenes under Friedel-Crafts conditions.
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    • The chloroenols 8 may be characterized by their oxidation number (Bellus, D.; Fischer, H.; Greuter, H.; Martin, P. Helv. Chim. Acta 1978, 61, 1784.)
    • The chloroenols 8 may be characterized by their "oxidation number" (Bellus, D.; Fischer, H.; Greuter, H.; Martin, P. Helv. Chim. Acta 1978, 61, 1784.)
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    • (ON 5) and may be regarded as derivatives of the hitherto unknown 1,4-dihydrosemisquaric acid II (ON 5). It must be pointed out that 1,4-dihydrosemisquaric acid II and semisquaric acid I (ON 6) posess the same oxidation numbers as hydroquinone (ON 5) and p-benzoquinone (ON 6). One further vinylogous acid having the ON 5, derives from semisquaric acid: the 1,2-dihydrosemisquaric acid III. Like II, acid III is also hitherto unknown. However, derivatives E. g.: Heerding, J. M.; Moore, H. W. J. Org. Chem. 1991, 56, 4048 of III have already been described. (Chemical Equation Presented)
    • (ON 5) and may be regarded as derivatives of the hitherto unknown 1,4-dihydrosemisquaric acid II (ON 5). It must be pointed out that 1,4-dihydrosemisquaric acid II and semisquaric acid I (ON 6) posess the same oxidation numbers as hydroquinone (ON 5) and p-benzoquinone (ON 6). One further vinylogous acid having the ON 5, derives from semisquaric acid: the 1,2-dihydrosemisquaric acid III. Like II, acid III is also hitherto unknown. However, derivatives E. g.: Heerding, J. M.; Moore, H. W. J. Org. Chem. 1991, 56, 4048 of III have already been described. (Chemical Equation Presented)
  • 33
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    • We are actively involved at the present time in finding out (a) conditions, (b) catalysts, and/or (c) substituent patterns of arenes 2 which allow the production of 3-arylcyclobutenediones 14 on a preparative scale by reacting 7 with 2.
    • We are actively involved at the present time in finding out (a) conditions, (b) catalysts, and/or (c) substituent patterns of arenes 2 which allow the production of 3-arylcyclobutenediones 14 on a preparative scale by reacting 7 with 2.
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    • For reviews on phenyl- and arylcyclobutenediones and their derivatives, see: a
    • For reviews on phenyl- and arylcyclobutenediones and their derivatives, see: (a) Ried, W.; Schmidt, A. H. Angew. Chem. 1972, 84, 1048.
    • (1972) Angew. Chem , vol.84 , pp. 1048
    • Ried, W.1    Schmidt, A.H.2
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    • For reviews on squaraines, see, a
    • For reviews on squaraines, see : (a) Sprenger, H. E.; Ziegenbein, W. Angew. Chem. 1968, 80, 541.
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    • Sprenger, H.E.1    Ziegenbein, W.2
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    • West, R, Ed, Academic Press: New York, Chapter 10, p
    • (c) Schmidt, A. H. In Oxocarbons, West, R., Ed.; Academic Press: New York, 1980; Chapter 10, p 185.
    • (1980) Oxocarbons , pp. 185
    • Schmidt, A.H.1
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    • The conversion of 2-(aroyloxy)-4-halogeno-3-aryl-2-cyclobuten-1-ones IVa into arylcyclobutenediones 14 by treatment with sulfuric acid (ref a) obviously occurs via IVb and offers early examples of the 3-halogeno [and 4-halogeno]-2-hydroxy-2-cyclobuten-1-one → cyclobutenedione conversion, including a halogenocyclobutane-1,2- dione as an intermediate. (a) Schmidt, A. H. Dissertation, Universität Frankfurt am Main, 1970.
    • The conversion of 2-(aroyloxy)-4-halogeno-3-aryl-2-cyclobuten-1-ones IVa into arylcyclobutenediones 14 by treatment with sulfuric acid (ref a) obviously occurs via IVb and offers early examples of the "3-halogeno [and 4-halogeno]-2-hydroxy-2-cyclobuten-1-one → cyclobutenedione conversion", including a halogenocyclobutane-1,2- dione as an intermediate. (a) Schmidt, A. H. Dissertation, Universität Frankfurt am Main, 1970.
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    • Ref 6a
    • (b) Ref 6a.
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    • For an application of this methodology, see
    • For an application of this methodology, see: Selwood, D. L.; Jandu, K. S. Heterocycles 1988, 27, 1191.
    • (1988) Heterocycles , vol.27 , pp. 1191
    • Selwood, D.L.1    Jandu, K.S.2
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    • For a review on the construction of complex organic molecules by thermally induced ring expansion of 4-hydroxy-2-cyclobuten-1-ones, see: Moore, H. W, Yerxa, B. R. Chemtracts: Org. Chem. 1992, 5, 273
    • For a review on the construction of complex organic molecules by thermally induced ring expansion of 4-hydroxy-2-cyclobuten-1-ones, see: Moore, H. W.; Yerxa, B. R. Chemtracts: Org. Chem. 1992, 5, 273.
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    • Improved procedure: (b) Schmidt, A. H.; Künz, Ch.; Debo, M.; Mora-Ferrer, J. P. Synthesis 1990, 819.
    • Improved procedure: (b) Schmidt, A. H.; Künz, Ch.; Debo, M.; Mora-Ferrer, J. P. Synthesis 1990, 819.


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