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1
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0029060845
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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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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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2
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76049124378
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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;
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5
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84982498470
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(c) Becher, H. J.; Fenske, D.; Langer, E. Chem Ber. 1973, 106, 177.
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(1973)
Chem Ber
, vol.106
, pp. 177
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Becher, H.J.1
Fenske, D.2
Langer, E.3
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0001087802
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(f) Wendling, L. A.; Koster, S. A.; Murray, J. E.; West, R. J. Org. Chem. 1977, 42, 1126.
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J. Org. Chem
, vol.42
, pp. 1126
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Wendling, L.A.1
Koster, S.A.2
Murray, J.E.3
West, R.4
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11
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76049128825
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3 (3 equiv). Yield 33%; mp 190-191 °C.
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3 (3 equiv). Yield 33%; mp 190-191 °C.
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12
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76049130050
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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
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(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.
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13
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76049100148
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Japanese Patent 62,249,953; 30 Oct, Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1988, 109, 170004r
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(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.
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(1987)
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Akasaki, Y.1
Tokida, A.2
Saeki, S.3
Torigoe, K.4
Imai, A.5
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14
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76049094578
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Japanese Patent 01,146,865; 8 June, Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1989, 111, 232571a
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(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.
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(1989)
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Akasaki, Y.1
Tokida, A.2
Torigoe, K.3
Imai, A.4
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15
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0025901636
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(m) Matsuoka, M; Soejima, H.; Kitao, T. Dyes and Pigments 1991, 16, 309.
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(1991)
Dyes and Pigments
, vol.16
, pp. 309
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Matsuoka, M.1
Soejima, H.2
Kitao, T.3
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17
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76049104626
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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.
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18
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76049099427
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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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19
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76049099656
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Japanese Patent 06,184,134; 5 July, Mitsubishi Chem. Ind, Japan. Chem. Abstr. 1995, 122, 105672m
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(b) Nakazumi, H. Japanese Patent 06,184,134; 5 July 1994; Mitsubishi Chem. Ind., Japan. Chem. Abstr. 1995, 122, 105672m.
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(1994)
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Nakazumi, H.1
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20
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76049120915
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Japanese Patent 06,100,511; 12. April 1994; Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1994, 121, 121397k
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(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.
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Nishikata, Y.1
Tomono, T.2
Fu, R.3
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21
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0000868849
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(d) Chen, H.; Herkstroeter, W. G.; Perlstein, J.; Law, K.-Y.; Whitten, D. G. J. Phys. Chem. 1994, 98, 5138.
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(1994)
J. Phys. Chem
, vol.98
, pp. 5138
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Chen, H.1
Herkstroeter, W.G.2
Perlstein, J.3
Law, K.-Y.4
Whitten, D.G.5
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22
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0027595521
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(e) Kitipichai, P.; La Peruta, R.; Korenowski, G. M.; Wnek, G. E. J. Polymer. Sci., Part A: Polym. Chem. 1993, 31, 1365.
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(1993)
J. Polymer. Sci., Part A: Polym. Chem
, vol.31
, pp. 1365
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Kitipichai, P.1
La Peruta, R.2
Korenowski, G.M.3
Wnek, G.E.4
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23
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76049103246
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Japanese Patent 04,202,166; 22. July 1992; Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1992, 117, 261281k
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(f) Fu, R. Japanese Patent 04,202,166; 22. July 1992; Fuji Xerox Co., Ltd., Japan; Chem. Abstr. 1992, 117, 261281k.
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Fu, R.1
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24
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76049107293
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Japanese Patent 04,202,165; 22 July, Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1992, 117, 261280j
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(g) Fu, R. Japanese Patent 04,202,165; 22 July 1992; Fuji Xerox Co., Ltd., Japan; Chem. Abstr. 1992, 117, 261280j.
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(1992)
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Fu, R.1
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25
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76049091852
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Japanese Patent 01,146,848; 8 June, Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1989, 111, 232276h
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(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.
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(1989)
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Akasaki, Y.1
Tokida, A.2
Torigoe, K.3
Imai, A.4
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26
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76049091615
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Japanese Patent 62,249,951; 30 Oct, Fuji Xerox Co, Ltd, Japan; Chem. Abstr. 1988, 109, 210668u
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(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.
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(1987)
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Akasaki, Y.1
Torigoe, K.2
Imai, A.3
Tokida, A.4
Saeki, S.5
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27
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84914401297
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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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28
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0004657206
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(a) Ried, W.; Schmidt, A. H.; Kuhn, W. Chem Ber. 1971, 104, 2622.
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(1971)
Chem Ber
, vol.104
, pp. 2622
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Ried, W.1
Schmidt, A.H.2
Kuhn, W.3
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29
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0001224767
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(b) Ried, W.; Knorr, H.; Kuhn, W.; Weissert, U. Chem Ber. 1975, 108, 1413.
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(1975)
Chem Ber
, vol.108
, pp. 1413
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Ried, W.1
Knorr, H.2
Kuhn, W.3
Weissert, U.4
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31
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0017803495
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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.)
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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.)
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32
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0042518340
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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)
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33
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76049090365
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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.
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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.
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34
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0037592558
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Smutny, E. J.; Caserio, M. C.; Roberts, J. D. J. Am. Chem. Soc. 1960, 82, 1793.
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(1960)
J. Am. Chem. Soc
, vol.82
, pp. 1793
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Smutny, E.J.1
Caserio, M.C.2
Roberts, J.D.3
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36
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1542453207
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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.
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(1972)
Angew. Chem
, vol.84
, pp. 1048
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Ried, W.1
Schmidt, A.H.2
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40
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0000181529
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For reviews on squaraines, see, a
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For reviews on squaraines, see : (a) Sprenger, H. E.; Ziegenbein, W. Angew. Chem. 1968, 80, 541.
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(1968)
Angew. Chem
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, pp. 541
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Sprenger, H.E.1
Ziegenbein, W.2
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43
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0012988324
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West, R, Ed, Academic Press: New York, Chapter 10, p
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(c) Schmidt, A. H. In Oxocarbons, West, R., Ed.; Academic Press: New York, 1980; Chapter 10, p 185.
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(1980)
Oxocarbons
, pp. 185
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Schmidt, A.H.1
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45
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76049102018
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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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46
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76049117910
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Ref 6a
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(b) Ref 6a.
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48
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0001429617
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For selected references, see: a
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For selected references, see: (a) Liebeskind, L. S.; Iyer, S.; Jewell, C. F., Jr. J. Org. Chem. 1986, 51, 3065.
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(1986)
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Liebeskind, L.S.1
Iyer, S.2
Jewell Jr., C.F.3
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(d) Liebeskind, L. S.; Granberg, K. L.; Zhang, J. J. Org. Chem. 1991, 57, 4345.
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Granberg, K.L.2
Zhang, J.3
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(e) Gurski Birchler, A.; Lin, F.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 7737.
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Lin, F.2
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For selected references, see: a
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For selected references, see: (a) Perri, S. T.; Foland, L. D.; Decker, O. H. W.; Moore, H. W. J. Org. Chem. 1986, 51, 3067.
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Foland, L.D.2
Decker, O.H.W.3
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(c) Perri, S. T.; Rice, P.; Moore, H. W. Org. Synth. 1990, 69, 220.
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(f) Gayo, L. M.; Winters, M. P.; Moore, H. W. J. Org. Chem. 1992, 57, 6896.
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For an application of this methodology, see
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For an application of this methodology, see: Selwood, D. L.; Jandu, K. S. Heterocycles 1988, 27, 1191.
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(1988)
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76049119666
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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
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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.
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Improved procedure: (b) Schmidt, A. H.; Künz, Ch.; Debo, M.; Mora-Ferrer, J. P. Synthesis 1990, 819.
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Improved procedure: (b) Schmidt, A. H.; Künz, Ch.; Debo, M.; Mora-Ferrer, J. P. Synthesis 1990, 819.
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Schmidt, A. H.; Künz, Ch.; Malmbak, M.; Zylla, J. Synthesis 1994, 422.
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