Thermal Generation of α,3-Dehydrotoluene from (Z)-1,2,4-Heptatrien-6-yne

Journal of the American Chemical Society

Volumn 111, Issue 20, 1989, Pages 8057-8059

  Myers, Andrew G ^a   Kuo, Elaine Y ^a   Finney, Nathaniel S ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001380819     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00202a079     Document Type: Article

References (7)

1. (a) Lee, M. D.; Dunne, T. S.; Siegel, M. M.; Chang, C. C.; Morton, G. O.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3464. (b) Lee, M. D.; Dunne, T. S.; Chang, C. C.; Ellestad, G. A.; Siegel, M. M.; Morton, G. O.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3466. (c) Golik, J.; Clardy, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3461. (d) Golik, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3462.
2. (a) Bergman, R. G.; Jones, R. R. J. Am. Chem. Soc. 1972, 94, 660. (b) Lockhart, T. P.; Comita, P. B.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4082. (c) Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091. (d) For a definition and discussion of the term dehydroaromatic”, see: Bergman, R. G. Acc. Chem. Res. 1973, 6, 25. (3) (a) Myers, A. G. Tetrahedron Lett. 1987, 28, 4493. (b) Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212. (c) Myers, A. G.; Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146.
3. 2X are known. X = cis-HC═CH: Ben-Efraim, D. A.; Sondheimer, F. Tetrahedron Lett. 1963, 313. X = O and S: Greenberg, M. M.; Blackstock, S. C.; Berson, J. A. Tetrahedron Lett. 1987, 28, 4263 and references therein.
4. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467. (b) Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313. (c) Use of cis-dichloroethylene in coupling reactions: Vollhardt, K. P. C.; Winn, L. S. Tetrahedron Lett. 1985, 26, 709. (d) Differential coupling of cis-dichloroethylene: Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631.
5. Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195.
6. Corey, E. J.; Wess, G.; Xiang, Y. B.; Singh, A. K. J. Am. Chem. Soc. 1987, 109, 4717.
7. (a) Myers, A. G.; Finney, N. S.; Kuo, E. Y. Tetrahedron Lett., in press. (b) Oxidative rearrangement of an allylic hydrazine has been accomplished with molecular oxygen; see ref 7. (c) For the oxidation of 1,1-and 1,2-di-alkylhydrazines, respectively, with diethyl azodicarboxylate, see: Fahr, E.; Koch, K.-H. Liebigs Ann. Chem. 1980, 219. Stone, K. J.; Greenberg, M. M.; Blackstock, S. C.; Berson, J. A. J. Am. Chem. Soc. 1989, 111, 3659.