Volume 41, Issue 16 pp. 2969-2971

Communication

1,2,3,5-Tetrahydro-1,2,3-methenopentalene, a Valence Isomer of Isoindene: Synthesis and Diels–Alder Reactions^†

Thomas Fischer Dr.,

Thomas Fischer Dr.

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Ulrike Kunz Dr.,

Ulrike Kunz Dr.

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Sarah E. Lackie,

Sarah E. Lackie

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Carsten Cohrs Dipl.-Chem.,

Carsten Cohrs Dipl.-Chem.

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Daniel D. Palmer,

Daniel D. Palmer

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Manfred Christl Prof.,

Manfred Christl Prof.

[email protected]

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Thomas Fischer Dr.,

Thomas Fischer Dr.

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Ulrike Kunz Dr.,

Ulrike Kunz Dr.

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Sarah E. Lackie,

Sarah E. Lackie

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Carsten Cohrs Dipl.-Chem.,

Carsten Cohrs Dipl.-Chem.

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Daniel D. Palmer,

Daniel D. Palmer

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

Manfred Christl Prof.,

Manfred Christl Prof.

[email protected]

Institut für Organische Chemie Universität Würzburg Am Hubland, 97074 Würzburg (Germany) Fax: (+49) 931-888-4606

Search for more papers by this author

First published: 21 August 2002

https://doi.org/10.1002/1521-3773(20020816)41:16<2969::AID-ANIE2969>3.0.CO;2-1

Citations: 8

^†

This work was supported by the Fonds der Chemischen Industrie and by Chemetall GmbH. S.E.L. and D.D.P. thank Heriot-Watt University, Edinburgh, and the European Community for an Erasmus exchange scholarship. Dipl.-Chem. Patrick Musch assisted us in the performance of the quantum-chemical calculations.

Share a link

Email
Wechat
Bluesky

Graphical Abstract

A strong pyramidalization of the double bond in the Diels–Alder adducts 3, as suggested by quantum-chemical calculations and NMR spectroscopic data, is probably the reason why these very reactive compounds are observable at best at low temperatures. The title compound 2, required for preparation of 3, was prepared in five steps from benzvalene 1.

References

1
1aP. D. Bartlett, A. J. Blakeney, G. L. Combs, J. Galloy, A. A. M. Roof, R. Subramanyam, W. H. Watson, W. J. Winter, C. Wu in Stereochemistry and Reactivity of Systems Containing π Electrons (Ed.: W. H. Watson), Verlag Chemie, Deerfield Beach, FL, 1983, pp. 75–104;
Google Scholar
1bP. D. Bartlett, C. Wu, J. Org. Chem. 1984, 49, 1880–1886;
10.1021/jo00185a007
CAS Web of Science® Google Scholar
1cP. D. Bartlett, C. Wu, J. Org. Chem. 1985, 50, 4087–4092.
10.1021/jo00221a024
CAS Web of Science® Google Scholar
2
2aL. A. Paquette in Stereochemistry and Reactivity of Systems Containing π Electrons (Ed.: W. H. Watson), Verlag Chemie, Deerfield Beach, FL, 1983, pp. 41–73;
Google Scholar
2bL. A. Paquette, H. Künzer, K. E. Green, O. De Lucchi, G. Licini, L. Pasquato, G. Valle, J. Am. Chem. Soc. 1986, 108, 3453–3460;
10.1021/ja00272a047
CAS Web of Science® Google Scholar
2cL. A. Paquette, C.-C. Shen, J. Am. Chem. Soc. 1990, 112, 1159–1164;
10.1021/ja00159a041
CAS Web of Science® Google Scholar
2dE. R. Hickey, L. A. Paquette, J. Am. Chem. Soc. 1995, 117, 163–176.
10.1021/ja00106a020
CAS Web of Science® Google Scholar
3F. Lanzendörfer, Dissertation, Universität Würzburg, 1984.
Google Scholar
4M. Christl, A. Kraft, Angew. Chem. 1988, 100, 1427–1428;
10.1002/ange.19881001036
CAS Google Scholar
Angew. Chem. Int. Ed. Engl. 1988, 27, 1369–1370.
10.1002/anie.198813691
Web of Science® Google Scholar
5A. Kraft, Dissertation, Universität Würzburg, 1989.
Google Scholar
6M. Christl, M. Türk, E.-M. Peters, K. Peters, H. G. von Schnering, Angew. Chem. 1994, 106, 1719–1720;
10.1002/ange.19941061535
CAS Google Scholar
Angew. Chem. Int. Ed. Engl. 1994, 33, 1639–1641.
10.1002/anie.199416391
Web of Science® Google Scholar
7M. Türk, Dissertation, Universität Würzburg, 1994.
Google Scholar
8T. Fischer, Dissertation, Universität Würzburg, 1996.
Google Scholar
9U. Kunz, S. Krimm, T. Fischer, T. Kottke, D. Stalke, M. Christl, Eur. J. Org. Chem. 1998, 2171–2176.
10.1002/(SICI)1099-0690(199810)1998:10<2171::AID-EJOC2171>3.0.CO;2-J
CAS Web of Science® Google Scholar
10U. Burger, B. Bianco, Helv. Chim. Acta 1983, 66, 60–67.
10.1002/hlca.19830660107
CAS Web of Science® Google Scholar
11
11aU. Burger, G. Gandillon, Tetrahedron Lett. 1979, 4281–4284;
10.1016/S0040-4039(01)86566-7
CAS Web of Science® Google Scholar
11bU. Burger, G. Gandillon, J. Mareda, Helv. Chim. Acta 1981, 64, 844–853.
10.1002/hlca.19810640323
CAS Web of Science® Google Scholar
12M. Christl, H. Reuchlein, Angew. Chem. 1990, 102, 1090–1091;
10.1002/ange.19901020927
CAS Google Scholar
Angew. Chem. Int. Ed. Engl. 1990, 29, 1035–1037.
10.1002/anie.199010351
Web of Science® Google Scholar
13S. H. Bertz, G. Dabbagh, J. Org. Chem. 1990, 55, 5161–5165.
10.1021/jo00304a033
CAS Web of Science® Google Scholar
14C. R. Saha-Möller, W. Adam in Comprehensive Heterocyclic Chemistry II, Vol. 1B (Ed ), Pergamon, Oxford, 1996, pp. 1041–1082.
10.1016/B978-008096518-5.00033-2
Google Scholar
15A. J. Bloodworth, D. S. Baker, J. Chem. Soc. Chem. Commun. 1981, 547–549.
10.1039/c39810000547
CAS Web of Science® Google Scholar
16
16aH. Leininger, M. Christl, D. Wendisch, Chem. Ber. 1983, 116, 681–689;
10.1002/cber.19831160226
CAS Web of Science® Google Scholar
16bK. Gollnick, A. Griesbeck, Tetrahedron Lett. 1984, 25, 725–728.
10.1016/S0040-4039(01)80010-1
CAS Web of Science® Google Scholar
17Gaussian 98 (Revision A.7), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
Google Scholar
18F. Lanzendörfer, M. Christl, Angew. Chem. 1983, 95, 896–897;
10.1002/ange.19830951112
Google Scholar
Angew. Chem. Int. Ed. Engl. 1983, 22, 871–872; different from the published value (3.0 Hz), the coupling constant between the central and the lateral bicyclo[1.1.0]butane protons of 21 has a value of only 1.5 Hz.
10.1002/anie.198308711
Web of Science® Google Scholar

Citing Literature

Volume41, Issue16

August 16, 2002

Pages 2969-2971

1,2,3,5-Tetrahydro-1,2,3-methenopentalene, a Valence Isomer of Isoindene: Synthesis and Diels–Alder Reactions^†

Graphical Abstract

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

1,2,3,5-Tetrahydro-1,2,3-methenopentalene, a Valence Isomer of Isoindene: Synthesis and Diels–Alder Reactions†

Graphical Abstract

References

Citing Literature

References

Related

Information

1,2,3,5-Tetrahydro-1,2,3-methenopentalene, a Valence Isomer of Isoindene: Synthesis and Diels–Alder Reactions^†