Synthesis and Structure of a Dimeric Peralkylated Hexaaminobenzene: Hexakis(dimethylamino)hexamethyl-hexaaza[63](1,3,5)cyclophane

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 6, 1997, Pages 621-623

  Wolff, J Jens ^a   Zietsch, Andreas ^a   Irngartinger, Hermann ^a   Oeser, Thomas ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Amines; Cyclophanes; Electron transfer

Indexed keywords

EID: 0030899960     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199706211     Document Type: Article

References (48)

1. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
2. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
3. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
4. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
5. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
6. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
7. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
8. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
9. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
10. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
11. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
12. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
13. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
14. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
15. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
16. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
17. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172; Angew. Chem. Int. Ed. Engl. 1993, 52, 1111-1129, and references therein; Reviews: M. A. Fox, Chem. Rev. 1992, 92, 365-368; N. Sutin, Prog. Inorg. Chem. 1983, 30, 441-498; L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987; J. K. Kochi, Angew. Chem. 1988, 100, 1331-1372; Angew. Chem. Int. Ed. Engl. 1988, 27, 1227-1266; Photoinduced Electron Transfer I-IV (Ed.: J. Mattay), Top. Curr. Chem. 1990-1992, 156, 158, 159, 163; J. Jortner, M. Bixon, J. Chem. Phys. 1988, 88, 167-170; T. Holstein, Philos. Mag. B 1978, 49-62, 499-526; G. Grampp, Angew. Chem. 1993, 105, 724-726; Angew. Chem. Int. Ed. Engl. 1993, 32, 691-693; H. Heitele, ibid. 1993, 105, 378-398 and 1993, 32, 359-377; W. R. Fawcett, M. Opallo, ibid. 1994, 106, 2239-2252 and 1994, 33, 2131-2143.
18. See for example G. Grampp, W. Jaenicke, Ber. Bunsenges. Phys. Chem. 1991, 95., 704-927; K. D. Jordan, M. N. Paddon-Row, Chem. Rev. 1992, 92, 395-410; H. Heitele, M. E. Michel-Beyerle, J. Am. Chem. Soc. 1985, 107, 8286-8288.
19. See for example G. Grampp, W. Jaenicke, Ber. Bunsenges. Phys. Chem. 1991, 95., 704-927; K. D. Jordan, M. N. Paddon-Row, Chem. Rev. 1992, 92, 395-410; H. Heitele, M. E. Michel-Beyerle, J. Am. Chem. Soc. 1985, 107, 8286-8288.
20. See for example G. Grampp, W. Jaenicke, Ber. Bunsenges. Phys. Chem. 1991, 95., 704-927; K. D. Jordan, M. N. Paddon-Row, Chem. Rev. 1992, 92, 395-410; H. Heitele, M. E. Michel-Beyerle, J. Am. Chem. Soc. 1985, 107, 8286-8288.
21. The inner reorganization energy is the amount of energy needed for the reorganization of all intramolecular coordinates during the ET process according to Marcus theory.
22. S. F. Nelsen, J. Adamus, J. J. Wolff, J. Am. Chem. Soc. 1994, 116, 1589-1590, and references therein.
23. a) K. Elbl, C. Krieger, H. A. Staab, Angew. Chem. 1986, 98, 1024-1026; Angew. Chem. Int. Ed. Engl. 1986, 25, 1023-1024;
24. a) K. Elbl, C. Krieger, H. A. Staab, Angew. Chem. 1986, 98, 1024-1026; Angew. Chem. Int. Ed. Engl. 1986, 25, 1023-1024;
25. b) J. M. Chance, B. Kahr, A. B. Buda, J. P. Toscano, K. Mislow, J. Org. Chem. 1988, 53, 3226-3232;
26. c) J. S. Miller, D. A. Dixon, J. C. Calabrese, C. Vazquez, P. J. Krusic, M. D. Ward, E. Wasserman, R. L. Harlow, J. Am. Chem. Soc. 1990, 112, 381-398;
27. d) J. Thomaides, P. Maslak, R. Breslow, ibid. 1988, 110, 3970-3979.
28. This follows from detailed cyclovoltammetric measurements on 3: B. Speiser, R. Mayer, M. Würde, Universität Tübingen, private communication; M. Würde, Diploma Thesis, Universität Tübingen, 1996. For the oxidation of 3, see also R. W. Johnson, Tetrahedron Lett. 1976, 17, 589-592; M. Dietrich, J. Heinze, J. Am. Chem. Soc. 1990, 112, 5142-5145; ref. [5b].
29. This follows from detailed cyclovoltammetric measurements on 3: B. Speiser, R. Mayer, M. Würde, Universität Tübingen, private communication; M. Würde, Diploma Thesis, Universität Tübingen, 1996. For the oxidation of 3, see also R. W. Johnson, Tetrahedron Lett. 1976, 17, 589-592; M. Dietrich, J. Heinze, J. Am. Chem. Soc. 1990, 112, 5142-5145; ref. [5b].
30. This follows from detailed cyclovoltammetric measurements on 3: B. Speiser, R. Mayer, M. Würde, Universität Tübingen, private communication; M. Würde, Diploma Thesis, Universität Tübingen, 1996. For the oxidation of 3, see also R. W. Johnson, Tetrahedron Lett. 1976, 17, 589-592; M. Dietrich, J. Heinze, J. Am. Chem. Soc. 1990, 112, 5142-5145; ref. [5b].
31. F. Vögtle, Cyclophan-Chemie, Teubner, Stuttgart, 1990, Chapter 5.5; P.M. Keehn, S. M. Rosenfeld, Cyclophanes, Academic Press, New York, 1983.
32. F. Vögtle, Cyclophan-Chemie, Teubner, Stuttgart, 1990, Chapter 5.5; P.M. Keehn, S. M. Rosenfeld, Cyclophanes, Academic Press, New York, 1983.
33. This was deduced from the presence of a CT band in the UV/Vis spectra of yellow-colored mixtures of 6 and and the model compound 3. Weak, crystalline 1:1 complexes of 6 with N,N-dimethylaniline (C. L. Jackson, L. Clarke, Ber. Dtsch. Chem. Ges. 1904, 37, 176-180) and of 6 and 1-naphthylamine (J. J. Sudborough, N. Picton, J. Chem. Soc. 1906, 89, 583-595), both brown in color, are known. The formation of a complex of 6 with hexamethylbenzene was inferred from the melting behavior of their yellow-colored mixtures: D. L. Hammick, A. Hellicar, J. Chem. Soc. 1938, 761-763.
34. This was deduced from the presence of a CT band in the UV/Vis spectra of yellow-colored mixtures of 6 and and the model compound 3. Weak, crystalline 1:1 complexes of 6 with N,N-dimethylaniline (C. L. Jackson, L. Clarke, Ber. Dtsch. Chem. Ges. 1904, 37, 176-180) and of 6 and 1-naphthylamine (J. J. Sudborough, N. Picton, J. Chem. Soc. 1906, 89, 583-595), both brown in color, are known. The formation of a complex of 6 with hexamethylbenzene was inferred from the melting behavior of their yellow-colored mixtures: D. L. Hammick, A. Hellicar, J. Chem. Soc. 1938, 761-763.
35. This was deduced from the presence of a CT band in the UV/Vis spectra of yellow-colored mixtures of 6 and and the model compound 3. Weak, crystalline 1:1 complexes of 6 with N,N-dimethylaniline (C. L. Jackson, L. Clarke, Ber. Dtsch. Chem. Ges. 1904, 37, 176-180) and of 6 and 1-naphthylamine (J. J. Sudborough, N. Picton, J. Chem. Soc. 1906, 89, 583-595), both brown in color, are known. The formation of a complex of 6 with hexamethylbenzene was inferred from the melting behavior of their yellow-colored mixtures: D. L. Hammick, A. Hellicar, J. Chem. Soc. 1938, 761-763.
36. J. J. Wolff, H. Irngartinger, F. Gredel, I. Bolocan, Chem. Ber. 1993, 126, 2127-2131, and references therein.
37. J. J. Wolff, F. Gredel, H. Irngartinger, Liebigs Ann. 1996, 1175-1182.
38. a) For the synthesis of a dimeric phloroglucinol comparable to 1 but not substituted in the nuclei, see W. D. Curtis, J. F. Stoddart, G. H. Jones, J. Chem. Soc. Perkin Trans. 1 1977, 785-788. For structural analyses of [6.6]paracyclophanes see
39. b) a tetramethoxytetraoxaparacyclophane with an interring distance of 4.012 Å: H. Bauer, J. Briaire, H. A. Staab, Tetrahedron Lett. 1985, 26, 6175-6178 (3% yield under high-dilution conditions);
40. 2 CH/-4 terephthalic acid-N,N′-dibenzylethylendiamide 1 with an interring distance of 5.321 Å; the distance is greater because the amide functions rigidify the chain: G. R. Newkome, L. E. Rogers, F. R. Fronczek, Acta Crystallogr. Sect. C 1993, 49, 1022-1024.
41. Molecular mechanics and semiempirical calculations of the structure of 1 give conformations that are close to those observed experimentally.
42. The van der Waals distance between two planar arenes amounts to ca. 3.4 Å (see also L. Pauling, The Nature of the Chemical Bond and the Structure of Molecules and Crystals, 3rd ed., Cornell University Press, Ithaca, 1960, p. 262).
43. -5 M).
44. P. Engelbertz (Chemische Fabrik Griesheim) D. R. P. 767510, 1936 [Chem. Abstr. 1955, 49, 14803d]; M. E. Hill, F. Taylor, Jr., J. Org. Chem. 1960, 25, 1037-1038. For the latter procedure, 266.5 g of oleum, not 266.5 mL as reported, are required.
45. P. Engelbertz (Chemische Fabrik Griesheim) D. R. P. 767510, 1936 [Chem. Abstr. 1955, 49, 14803d]; M. E. Hill, F. Taylor, Jr., J. Org. Chem. 1960, 25, 1037-1038. For the latter procedure, 266.5 g of oleum, not 266.5 mL as reported, are required.
46. H. Quast, W. Risler, G. Döllscher, Synthesis 1972, 558.
47. G. M. Sheldrick, SHELXS-86: Program for Crystal Structure Solution, Göttingen, 1986.
48. G. M. Sheldrick, SHELXL-93, Göttingen, 1993.