Incorporation of an Allene Unit into α-Pinene: Generation of the Cyclic Allene 2,7,7-Trimethylbicyclo[4.1.1]octa-2,3-diene and Its Dimerization

Journal of Organic Chemistry

Volumn 69, Issue 4, 2004, Pages 1202-1206

  Azizoǧlu, Akin ^b,c   Özen, Recep ^a,c   Hökelek, Tuncer ^d   Balci, Metin ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^b BALIKESIR UNIVERSITY   (Turkey)

^c MERSIN UNIVERSITY   (Turkey)

^d HACETTEPE UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; DIMERIZATION; ORGANOMETALLICS; PROBABILITY DENSITY FUNCTION;

CYCLODIMERIZATION;

OLEFINS;

2,7,7 TRIMETHYLBICYCLO[4.1.1]OCTA 2,3 DIENE; 3,3 DIBROMO 2,7,7 TRIMETHYLTRICYCLO[4.1.1.0]OCTANE; ALLENE DERIVATIVE; CARBENOID; DIMER; LITHIUM DERIVATIVE; OCTANE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; CYCLIZATION; DENSITY FUNCTIONAL THEORY; DIMERIZATION; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS;

ALKADIENES; BICYCLO COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOTERPENES; THERMODYNAMICS;

EID: 10744231749     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035450z     Document Type: Article

References (32)

1. (a) Balci, M.; Taskesenligil, Y. In Advances in Strained and Interesting Organic Molecules; Halton, B., Ed.; JAI Press Inc: Stamfort, CT, 2000; Vol. 8, pp 43-81.
2. (b) Johnson, R. P. Chem. Rev. 1989, 89, 1111-1124.
3. (a) Engels, B.; Schoneboom, J. C.; Munster, A. F.; Groetsch, S.; Christl, M. J. Am. Chem. Soc. 2002, 124, 287-297.
4. (b) Nendel, M.; Tolbert, L. M.; Herring, L. A.; Islam, Md. N.; Houk, K. N. J. Org. Chem. 1999, 64, 976-983.
5. (c) Angus, R. O., Jr.; Schmidt, M. W. J. Am. Chem. Soc. 1985, 107, 532-537.
6. (d) Yavari, I.; Nori-Shargh, D.; Najafian, K. J. Mol. Struct.: THEOCHEM 1999, 467, 147-152.
7. For very recent synthesis of some cyclic strained allenes see: (a) Ogawa, K.; Okazaki, T.; Kinoshita, T. J. Org. Chem. 2003, 68, 1579-1581.
8. (b) Algi, F.; Ozen, R.; Balci, M. Tetrahedron Lett. 2002, 43, 3129-3131.
9. (c) Ozen, R.; Balci, M. Tetrahedron 2002, 58, 3079-3083.
10. (a) Moore, W. R.; Ward, H. R. J. Org. Chem. 1960, 25, 2073.
11. (b) Moore, W. R.; King, B. J. J. Org. Chem. 1971, 36, 1877-1882.
12. (a) Skattebol, L. Tetrahedron Lett. 1961, 167-172.
13. (b) Skattebol, L. Acta Chem. Scand. 1963, 17, 1683.
14. (a) Sydnes, L. K. Chem. Rev. 2003, 103, 1133-1150.
15. (b) Fedorynski, M. Chem. Rev. 2003, 103, 1099-1132.
16. (a) Doering, W. v. E.; LaFlamme, P. M. Tetrahedron 1958, 2, 75-79.
17. (b) Christl, M.; Groetsch, S.; Günther, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 3261-3263.
18. (c) Tolbert, M. L.; Islam, M. N.; Johnson, R. P.; Loisella, P. M.; Shakespeare, W. C. J. Am. Chem. Soc. 1990, 112, 6416-6417.
19. (d) Christl, M.; Schreck, M. Chem. Ber. 1987, 120, 915-920.
20. (e) Christl, M.; Braun, M. Chem. Ber. 1989, 122, 1939-1946.
21. (f) Christl, M.; Braun, M.; Wagner, W. Chem. Ber. 1994, 127, 1137-1142.
22. Baird, M. S.; Sadler, P.; Hatem, J.; Zahra, J.-P.; Waegell, B. J. Chem. Soc., Chem. Commun. 1979, 452-453.
23. Moore, W. R.; Moser, W. R. J. Am. Chem. Soc. 1970, 92, 5469-5474.
24. (a) Moore, W. R.; Ward, H. R.; Merritt, R. F. J. Am. Chem. Soc. 1961, 83, 2019-2020.
25. (b) Köbrich, G.; Goyert, W. Tetrahedron 1968, 24, 4327-4342.
26. Paquette, L. A.; Taylor, R. T. J. Am. Chem. Soc. 1977, 99, 5708-5715.
27. Bettinger, H. F.; Schleyer, P. v. R.; Schreiner, P. R.; Schaefer, H. F. III J. Org. Chem. 1997, 62, 9267-9275.
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle E. S.; Pople, J. A. Gaussian 98, Revision A.8; Gaussian, Inc., Pittsburgh, PA, 1998.
29. For the chemistry of cyclopropylidenes see: Backes, J.; Brinker, U. H. In Houben-Weyl (Methoden der Organischen Chemie); Regitz, M., Ed.; Thieme: Stuttgart, Germany, 1989; Vol. E 19b, pp 391-510.
30. (a) Hatem, J.; Waegell, B. Tetrahedron 1990, 46, 2789-2806.
31. (b) Hatem, J.; Waegell, B. Tetrahedron Lett. 1973, 23, 2023-2026.
32. (c) Graefe, J.; Thank, L. M.; Muehlstaedt, M. Z. Chem. 1971, 11, 252-253.