Electrochemical oxidation of cyclooctatetraene in the presence of allyltrimethylsilane. Anodic trialkylation with bicyclization

Tetrahedron Letters

Volumn 53, Issue 9, 2012, Pages 1015-1017

  Bours, Justin ^a   Morton, Martha ^b   Fry, Albert J ^a  

^a WESLEYAN UNIVERSITY   (United States)

^b UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

silyl cation; Anodic oxidation; Carbocationic cyclization; Cyclooctatetraene; Homotropylium ion

Indexed keywords

ACETONITRILE; ALICYCLIC COMPOUND; ALLYLTRIMETHYLSILANE; CATION; CYCLOOCTATETRAENE; UNCLASSIFIED DRUG;

ALKYLATION; ANODIC TRIALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTROCHEMICAL OXIDATION; ELECTROCHEMISTRY; NUCLEOPHILICITY; OXIDATION;

EID: 84856232808     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.072     Document Type: Article

References (24)

1. M.J. Shaw, J. Hyde, C. White, and W.E. Geiger Organometallics 23 2004 2205
2. L.A. Paquette Tetrahedron 31 1975 2855
3. A.J. Fry Electroanalysis 18 2006 391
4. A.J. Fry A.J. Fry, W.E. Britton, Topics in Organic Electrochemistry 1986 Plenum New York
5. B.J. Huebert, and D.E. Smith J. Electroanal. Chem. 31 1971 333
6. L. Eberson, K. Nyberg, M. Finkelstein, R.C. Petersen, and S.D. Ross J. Org. Chem. 32 1967 16
7. G. Connors, X. Wu, and A.J. Fry Org. Lett. 9 2007 1671
8. R. Huisgen, G. Boche, A. Dahmen, and W. Hechtl Tetrahedron Lett. 9 1968 5215
9. A.J. Fry Tetrahedron 64 2008 2101
10. I. Fleming, J. Dunogués, and R. Smithers Org. React. 37 1989 57
11. M. Brookhart, M. Ogliaruso, and S. Winstein J. Am. Chem. Soc. 89 1967 1965
12. S. Winstein Special Publication, Chemical Society 21 1967 5
13. C. Lepetit, B. Silvi, and R. Chauvin J. Phys. Chem. A 107 2003 464
14. D. Cremer, F. Reichel, and E. Kraka J. Am. Chem. Soc. 113 1991 9459
15. R.C. Haddon J. Am. Chem. Soc. 110 1988 1108
16. S. Winstein, and R. Adams J. Am. Chem. Soc. 70 1948 838
17. J. Japenga, G.W. Klumpp, and J. Stapersma Tetrahedron 33 1977 2847
18. P.M. Warner, S.-C. Chang, and N.J. Koszewski Tetrahedron Lett. 26 1985 5371
19. Akiyama, T.; Asayama, K.; Fujiyoshi, S. J. Chem. Soc. Perkin I 1998, 3655
20. S. Brocherieux-Lanoy, H. Dhimane, J. Poupon, C. Vannucci, and G. Lhommet J. Chem. Soc. Perkin I 1997 2163
21. G.S. Hammond, F.J. Modic, and R.M. Hedges J. Am. Chem. Soc. 75 1953 1388
22. K.A. Kobe, and H. Levin Ind. Eng. Chem. 42 1950 352
23. R.D. Kleene J. Am. Chem. Soc. 71 1949 2259
24. P.C. Lambert, and A.J. Fry Tetrahedron Lett. 52 2011 5281