Preparation of 1,4,5,8-tetra-tert-butyl-1,3,5,7-cyclooctatetraene by twofold SO2 extrusion

Tetrahedron Letters

Volumn 44, Issue 43, 2003, Pages 7893-7896

  Takayama, Jun ^a   Sugihara, Yoshiaki ^a   Ishii, Akihiko ^a   Nakayama, Juzo ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

Cyclooctatetraene; DFT calculations; Extrusion of SO2; Steric congestion; X ray crystallographic analysis

Indexed keywords

1,4,5,8 TETRA TERT BUTYL 1,3,5,7 CYCLOOCTATETRAENE; 2 (3,4,7,8 TETRA TERT BUTYL) 9,10 DITHIATRICYCLO[4.2.1.1 2,5 ]DECA 3,7 DIENE 9,10 DIOXIDE; ALKENE DERIVATIVE; DIMETHYLDIOXIRANE; OXIDE; SULFATE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; MOLECULAR DYNAMICS; OXIDATION; QUANTITATIVE ANALYSIS; SYNTHESIS; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 0141648299     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.014     Document Type: Article

References (30)

1. Nakayama J., Yamaoka S., Nakanishi T., Hoshino M. J. Am. Chem. Soc. 110:1988;6598.
2. Nakayama J., Hirashima A. J. Am. Chem. Soc. 112:1990;7648.
3. Nakayama J., Sugihara Y., Terada K., Clennan E.L. Tetrahedron Lett. 31:1990;4473.
4. Nakayama J., Hasemi R., Yoshimura K., Sugihara Y., Yamaoka S., Nakamura N. J. Org. Chem. 63:1998;4912.
5. Nakayama J. Bull. Chem. Soc. Jpn. 73:2000;1.
6. Otani T., Takayama J., Sugihara Y., Ishii A., Nakayama J. J. Am. Chem. Soc. 125:2003;8255.
7. Nakayama J., Yamaoka S., Hoshino M. Tetrahedron Lett. 29:1988;1161.
8. Nakayama J., Yu T., Sugihara Y., Ishii A. Chem. Lett. 1997;499.
9. We thank Professor Naoki Inamoto for his kind suggestion of this nomenclature.
10. Nakayama J., Takayama J., Sugihara Y., Ishii A. Chem. Lett. 2001;758.
11. Chemistry of multi-tert-butyl substituted cyclooctatetraenes. (a) Synthesis of 1,4-di- and 1,3,5,7-tetra-tert-butylcyclooctateraenes; Miller, M. J.; Lyttle, M. H.; Streitwieser, A., Jr. J. Org. Chem. 1981, 46, 1977; (b) Synthesis and absolute configuration of the enantiomeric 1,3-di-tert-butylcyclooctatetraenes; Paquette, L. A.; Hanzawa, Y.; McCullough, K. J.; Tagle, B.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 2262; (c) Unsucessful synthesis of 1,2-di-tert-butyl-1,3,5,7-cyclooctatetraene by photolysis of 7,8-di-tert-butylbicylo[4.2.0]octa-2,4,7-triene; Hanzawa, Y.; Paquette, L. A.; J. Am. Chem. Soc. 1981, 103, 2269; (d) Synthesis of and bond shifting equlibrium between 1,4- and 1,6-di-tert-butylcyclooctatetraenes; Paquette, L. A.; Hefferon, G. J.; Samodral, R.; Hanzawa, Y. J. Org. Chem. 1983, 48, 1262; (e) Synthesis of 1,3,5,7-tert-butylcyclooctatetraene; Boussie, T. R.; Streitwieser, A. J. Org. Chem. 1993, 58, 2377.
12. Chemistry of multi-tert-butyl substituted cyclooctatetraenes. (a) Synthesis of 1,4-di- and 1,3,5,7-tetra-tert-butylcyclooctateraenes; Miller, M. J.; Lyttle, M. H.; Streitwieser, A., Jr. J. Org. Chem. 1981, 46, 1977; (b) Synthesis and absolute configuration of the enantiomeric 1,3-di-tert-butylcyclooctatetraenes; Paquette, L. A.; Hanzawa, Y.; McCullough, K. J.; Tagle, B.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 2262; (c) Unsucessful synthesis of 1,2-di-tert-butyl-1,3,5,7-cyclooctatetraene by photolysis of 7,8-di-tert-butylbicylo[4.2.0]octa-2,4,7-triene; Hanzawa, Y.; Paquette, L. A.; J. Am. Chem. Soc. 1981, 103, 2269; (d) Synthesis of and bond shifting equlibrium between 1,4- and 1,6-di-tert-butylcyclooctatetraenes; Paquette, L. A.; Hefferon, G. J.; Samodral, R.; Hanzawa, Y. J. Org. Chem. 1983, 48, 1262; (e) Synthesis of 1,3,5,7-tert-butylcyclooctatetraene; Boussie, T. R.; Streitwieser, A. J. Org. Chem. 1993, 58, 2377.
13. Chemistry of multi-tert-butyl substituted cyclooctatetraenes. (a) Synthesis of 1,4-di- and 1,3,5,7-tetra-tert-butylcyclooctateraenes; Miller, M. J.; Lyttle, M. H.; Streitwieser, A., Jr. J. Org. Chem. 1981, 46, 1977; (b) Synthesis and absolute configuration of the enantiomeric 1,3-di-tert-butylcyclooctatetraenes; Paquette, L. A.; Hanzawa, Y.; McCullough, K. J.; Tagle, B.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 2262; (c) Unsucessful synthesis of 1,2-di-tert-butyl-1,3,5,7-cyclooctatetraene by photolysis of 7,8-di-tert-butylbicylo[4.2.0]octa-2,4,7-triene; Hanzawa, Y.; Paquette, L. A.; J. Am. Chem. Soc. 1981, 103, 2269; (d) Synthesis of and bond shifting equlibrium between 1,4- and 1,6-di-tert-butylcyclooctatetraenes; Paquette, L. A.; Hefferon, G. J.; Samodral, R.; Hanzawa, Y. J. Org. Chem. 1983, 48, 1262; (e) Synthesis of 1,3,5,7-tert-butylcyclooctatetraene; Boussie, T. R.; Streitwieser, A. J. Org. Chem. 1993, 58, 2377.
14. Chemistry of multi-tert-butyl substituted cyclooctatetraenes. (a) Synthesis of 1,4-di- and 1,3,5,7-tetra-tert-butylcyclooctateraenes; Miller, M. J.; Lyttle, M. H.; Streitwieser, A., Jr. J. Org. Chem. 1981, 46, 1977; (b) Synthesis and absolute configuration of the enantiomeric 1,3-di-tert-butylcyclooctatetraenes; Paquette, L. A.; Hanzawa, Y.; McCullough, K. J.; Tagle, B.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 2262; (c) Unsucessful synthesis of 1,2-di-tert-butyl-1,3,5,7-cyclooctatetraene by photolysis of 7,8-di-tert-butylbicylo[4.2.0]octa-2,4,7-triene; Hanzawa, Y.; Paquette, L. A.; J. Am. Chem. Soc. 1981, 103, 2269; (d) Synthesis of and bond shifting equlibrium between 1,4- and 1,6-di-tert-butylcyclooctatetraenes; Paquette, L. A.; Hefferon, G. J.; Samodral, R.; Hanzawa, Y. J. Org. Chem. 1983, 48, 1262; (e) Synthesis of 1,3,5,7-tert-butylcyclooctatetraene; Boussie, T. R.; Streitwieser, A. J. Org. Chem. 1993, 58, 2377.
15. Chemistry of multi-tert-butyl substituted cyclooctatetraenes. (a) Synthesis of 1,4-di- and 1,3,5,7-tetra-tert-butylcyclooctateraenes; Miller, M. J.; Lyttle, M. H.; Streitwieser, A., Jr. J. Org. Chem. 1981, 46, 1977; (b) Synthesis and absolute configuration of the enantiomeric 1,3-di-tert-butylcyclooctatetraenes; Paquette, L. A.; Hanzawa, Y.; McCullough, K. J.; Tagle, B.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 2262; (c) Unsucessful synthesis of 1,2-di-tert-butyl-1,3,5,7-cyclooctatetraene by photolysis of 7,8-di-tert-butylbicylo[4.2.0]octa-2,4,7-triene; Hanzawa, Y.; Paquette, L. A.; J. Am. Chem. Soc. 1981, 103, 2269; (d) Synthesis of and bond shifting equlibrium between 1,4- and 1,6-di-tert-butylcyclooctatetraenes; Paquette, L. A.; Hefferon, G. J.; Samodral, R.; Hanzawa, Y. J. Org. Chem. 1983, 48, 1262; (e) Synthesis of 1,3,5,7-tert-butylcyclooctatetraene; Boussie, T. R.; Streitwieser, A. J. Org. Chem. 1993, 58, 2377.
16. Tetra-tert-butylcyclooctatetraene 6 was obtained in the laboratory of Professor G. Maier by photolysis of 3,4-di-tert-butylcyclobutene-1,2-dicarboxylic acid anhydride; Fritschi, G., Ph.D. Thesis, 1971, Karlsruhe, Germany. Photolysis of the above anhydride produced five hydrocarbons of similar polarity containing 6 (in about 2% yield), in addition to two ketones. It was suggested that 1,4,5,8-tetra-tert-butylcyclooctatetraene ( 6a ) is sterically a more stable isomer than 1,2,5,6-tert-butylcyclooctatetraene ( 6c ).
17. Cyclooctatetraene 6 is not registered in Chemical Abstracts. We thank Professor A. Krebs of Hamburg University for providing us the information given in Ref. 7.
18. 2=0.103 (all), S=0.709.
19. Oxidation of 2 with m-chloroperbenzoic acid is sluggish and gave a complex mixture.
20. 3) δ=32.3, 35.4, 126.3, 151.4.
21. Nakayama J., Machida H., Saito R., Akimoto K., Hoshino M. Chem. Lett. 1985;1173. and references cited therein.
22. For preparation of the parent compound of this ring system, see (a) Gasteiger, J.; Huisgen R.; J. Am. Chem. Soc. 1972, 94, 6541; (b) Paquette L. A. ; Meisinger, R. H.; Wingard, R. E., Jr. J. Am. Chem. Soc. 1973, 95, 2230.
23. For preparation of the parent compound of this ring system, see (a) Gasteiger, J.; Huisgen R.; J. Am. Chem. Soc. 1972, 94, 6541; (b) Paquette L. A. ; Meisinger, R. H.; Wingard, R. E., Jr. J. Am. Chem. Soc. 1973, 95, 2230.
24. 13b See also: Rigby J.H., Warshakoon N.C. Tetrahedron Lett. 38:1997;2049.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98 Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
26. Paquette L.A. Tetrahedron. 31:1975;2855.
27. Fray G.I., Saxton R.G. The Chemistry of Cylooctatetraene and Its Derivatives. 1978;Cambridge University Press, New York.
28. Angle modification of 126° to approximately 136° is required: Allinger, N. L.; Sprague, J. T.; Finder, C. J. Tetrahedron 1973, 29, 2519. The calculated internal bonds angles for 6a are in the range 118.8-125.7° and for the experimental values, see Figure 4.
29. 2=0.1595 (all), S=1.174, T=153 K.
30. X-Ray crystallographic analysis of 1,4,5,8-tetrakis[(p-tolyloxy)methyl]-1,3,5,7-cyclooctatetranene was reported. See: Diercks R., Stamp L., tom Dieck H. Chem. Ber. 117:1984;1913.