Formation of Olefins via Pyrolysis of Sulfonate Esters

Journal of Organic Chemistry

Volumn 54, Issue 2, 1989, Pages 389-393

  Corey, E J ^a   Posner, Gary H ^b   Atkinson, Richard F ^c   Wingard, Astrid K ^c   Halloran, Daniel J ^c   Radzik, Donna M ^c   Nash, John J ^c  

^a HARVARD UNIVERSITY   (United States)

^b JOHNS HOPKINS UNIVERSITY   (United States)

^c GRAND VALLEY STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001389361     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00263a024     Document Type: Article

References (8)

1. This work was supported in a grant from the Research and Scholarly Development Committee of Grand Valley State University.
2. Foldi, Z. Chem. Ber. 1927, 60, 656. (b) Drahowzal, F.; Klamann, D. Monatsh. Chem. 1951, 82, 467. (c) Gough, G. A. C.; Hunter, H.; Kenyon, J. J. Chem. Soc. 1926, 2066.
3. DePuy, C. H.; King, E. R. Chem. Rev. 1960, 60, 431. (b) Cope, A. C.; Trumbull, E. R. Org. React. 1960, 11, 317.
4. See: (a) Huckel, W.; Rucker, D. Ann. Chem. 1963, 666, 30. (b) Cope, A. C.; Acton, E. M. J. Am. Chem. Soc. 1958, 80, 1955.
5. Elimination from neomenthylammonium hydroxide in water by an El mechanism gives 98% of 3-menthene and 2% of 2-menthene. The reaction of menthylammonium hydroxide gives 14% of 3-menthene and 86% of 2-menthene. Huges, E. D.; Wilby, J. J. Chem. Soc. 1960, 4094. (6) (a) Kwart, H.; Takeshita, T.; Nyce, J. L. J. Am. Chem. Soc. 1964, 86, 2606.
6. The E2 elimination of menthyl chloride with NaOEt gives only 2-menthene. (a) Hughes, E. D.; Ingold, C. K.; Rose, J. B. J. Chem. Soc. 1953, 3839. (b) Huckel, W.; Tappe, W.; Legutke, G. Ann. Chem. 1940, 543, 191.
7. Boggiano, B. G.; Petrow, V.; Stephenson, O.; Wild, A. M. J. Pharm. Pharmacol. 1961, 13, 567. (b) Hurd, C. D.; Morrissey, C. J. J. Am. Chem. Soc. 1955, 77, 4658.
8. Fuerst, H.; Heltzig, M.; Goebel W. J. Prakt. Chem. 1967, 36, 160. (b) Machek, G. Monatsh. Chem. 1938, 72, 77.