An Efficient and Versatile Generation of o-Xylylenes by Fluoride Anion Induced 1,4 Elimination of o-(α-Trimethylsilylalkyl)benzyltrimethylammonium Halides

Journal of the American Chemical Society

Volumn 102, Issue 2, 1980, Pages 863-865

  Ito, Yoshihiko ^a   Nakatsuka, Masashi ^a   Saegusa, Takeo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001271709     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00522a081     Document Type: Article

References (20)

1. Cava, M. P.; Diera, A. A.; Muth, K. J. Am. Chem. Soc. 1959, 81, 6458.
2. Alder, K.; Fremery, M. Tetrahedron 1961, 14, 190.
3. Slsido, K.; Kusano, N.; Noyori, R.; Nozaki, Y.; Slmosaka, M.; Nozaki, H. J. Polymer Sci. 1963, 1, 2101.
4. Nozaki, H.; Noyori, R. Tetrahedron 1966, 22, 2163.
5. Ito, Y.; Yonezawa, K.; Saegusa, T. J. Org. Chem. 1974, 39, 2769.
6. Errede, L. A. J. Am. Chem. Soc. 1961, 83, 949.
7. Oppolzer, W. J. Am. Chem. Soc. 1971, 93, 3833.
8. Oppolzer, W.; Keller, K. J. Am. Chem. Soc. 1971, 93, 3836.
9. Funk, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1976, 98, 6755.
10. Funk, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 5483.
11. Kametanl, T.; Nemoto, H.; Ishikawa, H.; Shlroyama, K.; Matsumoto, H.; Fukumoto, K., J. Am. Chem. Soc. 1977, 99, 3461.
12. For a review, see Oppolzer, W. Synthesis 1978, 793.
13. It is known that fluoride anion promotes β elimination of halosilane leading to strained alkene and behzyne: Cunico, R. F.; Dexhelmer, E. M. J. Organomet. Chem. 1973, 59, 153.
14. Chan, T. H.; Massuda, D. J. Am. Chem. Soc. 1977, 99, 936.
15. Compound 5 was Identified as the splro[di-o-xylylene] 5 by comparison of its NMR and IR spectra with those reported by Errede. 2
16. Brasen, W. R.; Hauser, C. R. “Organic Syntheses”; Wiley: New York, 1963; Collect. Vol. IV, p 585.
17. Jones, F. N.; Zinn, M. F.; Hauser, C. R. J. Org. Chem. 1963, 28, 663.
18. Structure A was assigned to compound 9 on the basis of Its IR and NMR spectra: IR (neat) 1640, 995, 909, 755 cm-1; NMR (CDCI3 with Me4Si) 1.0-3.0 (m, 21 H), 4.6-6.5 (m, 11 H), 6.9-7.2 (m, 4). A possibility of the regiolsomeric structure
19. for 9 was excluded by lack of IR absorption band at 890 cm-1 characters of the exo-methylene structure.
20. Dehydrogenation of 3-iv by palladium on charcoal gave 1-methyl-2-cyanonaphthalene. 3-iv: NMR (CDCI3 with Me4SI) 1.45 (d, 3), 1.8-2.3 (m, 2 H), 2.6-3.3 (m, 4), 7.05 (br s, 4 H).