Schmitz, C.
Harvey, JN.
Viehe, HG.
The known ene-type addition of thionium ions to alkenes has now been applied to the synthesis of homoallylic sulfides, from thionium ions RHC = S+Ar (R = alkyl, Ar = 4-chlorophenyl) and propene or other unactivated alkenes. Oxidation and thermal dehydrosulfenylation then lead to conjugated dienes. Because the reaction conditions are compatible with many functional groups, this method is simple and useful.
- Sulfur-Containing Carbocations, Organic Chemistry: A Series of Monographs (1978) ISBN:9780121070502 p.128-175, 10.1016/b978-0-12-107050-2.50012-2
- Claus, Methoden der organischen Chemie, E11, 1469 (1985)
- Smit, Organic Chemistry of Sulfur, 141 (1990)
- Hevesi, Bull. Soc. Chim. Fr., 127, 697 (1990)
- Ishibashi, Rev. Heteroatom Chem., 7, 191 (1992)
- Chem. Abstr., 118, 101679p (1993)
- Apeloig Yitzhak, Karni Miriam, The stabilities of α-oxy and α-thio carbenium ions: the importance of the ground-state energies of the neutral precursors, 10.1039/p29880000625
- Modena Giorgio, Scorrano Gianfranco, Venturello Paolo, Stability of α-sulphur- and α-oxygen-substituted carbonium ions, 10.1039/p29790000001
- Jagannadham, J. Am. Chem. Soc., 115, 8465 (1993)
- K. Hartke E. Akgün Lieb. Ann. Chem. 47 51 1981
- De Lucchi, Org. React., 40, 157 (1991)
- T. Takeda Y. Kaneko H. Nakagawa T. Fujiwara Chem. Lett. 1963 1966 1987
- Dilworth, Tetrahedron, 42, 3731 (1986)
- Mann, Tetrahedron Lett., 29, 6175 (1988)
- Mori, J. Org. Chem., 55, 5966 (1990)
- Simpkins, Tetrahedron, 47, 323 (1991)
- N. Ono Tuo Xiao Jun T. Hashimoto A. Kaji. J. Chem. Soc., Chem. Commun. 947 948 1987
- Sato, J. Org. Chem., 55, 6116 (1990)
- Hagen, J. Am. Chem. Soc., 113, 4954 (1991)
- Mayr, Angew. Chem., Int. Ed. Engl, 29, 1371 (1990)
- Mayr, Angew. Chem., Int. Ed. Engl, 31, 1613 (1992)
- Gross, Chem. Ber., 97, 2606 (1964)
- G. A. Olah G. Neyer Synthesis 276 278 1994
- Paterson, Tetrahedron Lett., 20, 2179 (1979)
- L. N. Mander P. H. C. Mundill Synthesis 620 622 1981
- Tamura, Tetrahedron Lett., 22, 1343 (1981)
- Mcintosh, Can. J. Chem., 63, 3313 (1985)
- H. Ishibashi T. Sato M. Irie M. Ito M. Ikeda J. Chem. Soc., Perkin Trans. I 1095 1098 1987
- Ishibashi, Synth. Commun., 19, 857 (1989)
- Brichard, Tetrahedron Lett., 33, 2511 (1992)
- Harvey, J. Chem. Soc., Perkin Trans., 1, 2275 (1993)
- Craig, Tetrahedron, 49, 11263 (1993)
- The reaction with the corresponding unsubstituted phenyl sulfide gives lower yields
- Mudryk, J. Am. Chem. Soc., 115, 3855 (1993)
- Ishibashi, Tetrahedron Lett., 26, 5791 (1985)
- Trost, Chem. Rev., 78, 363 (1978)
- Overman, Acc Chem. Res., 25, 352 (1992)
- K. Mikami H. Kishino J. Chem. Soc., Chem. Commun. 1843 1844 1993
- Blumenkopf, J. Am. Chem. Soc., 112, 4399 (1990)
- Cohen, J. Org. Chem., 48, 4531 (1983)
- Snider, Acc. Chem. Res., 13, 426 (1980)
- Snider, Comprehensive Organic Synthesis, 2, 567 (1991)
- Mikami, Chem. Rev., 92, 1021 (1992)
- Song, J. Am. Chem. Soc., 112, 8126 (1990)
- Marshall, J. Org. Chem, 57, 5851 (1992)
- Ishibashi, Heterocycles, 31, 215 (1990)
- NAKATANI Hiroshi, SO Taru Su, ISHIBASHI Hiroyuki, IKEDA Masazumi, Synthesis of thiochromans by means of a (4++2) polar cycloaddition of m-tolylthiomethyl chloride with substituted alkenes: A simple synthesis of (.+-.)-cuparene and related sesquiterpenoids., 10.1248/cpb.38.1233
- H. Ishibashi S. Harada M. Okada M. Ikeda K. Ishiyama H. Yamashita Y. Tamura Synthesis 847 849 1986
- Ishibashi, J. Chem. Soc., Perkin Trans., 1, 1099 (1987)
- SATO Tatsunori, ITO Tamiko, ISHIBASHI Hiroyuki, IKEDA Masazumi, New entries to 2(1H)-quinolinones and 2H-1-benzazepin-2-ones by acid-catalyzed olefin cyclization of N-(o-(alk-1-enyl)phenyl)-2-(methylsulfinyl)acetamides., 10.1248/cpb.38.3331
- Zhuzbaev, Izv. Akad. Nauk. SSSR, Ser. Khim., 1569 (1991)
- Chem. Abstr., 116, 20697z (1992)
- Coldham, J. Chem. Soc., Perkin Trans., 1, 1637 (1993)
- Giese, Chem. Ber., 114, 2859 (1981)
- Masaki, Tetrahedron, 40, 3481 (1984)
- Kudo, Tetrahedron Lett., 34, 7063 (1993)
- Eliel, Tetrahedron Lett., 21, 331 (1980)
- Eliel, J. Am. Chem. Soc., 107, 2946 (1985)
- Watanabe, J. Org. Chem., 54, 4088 (1989)
- Hudlicky, J. Org. Chem., 46, 2911 (1981)
- Anikin, Makromol. Chem., 194, 2663 (1993)
- Laschewsky, Macromolecules, 21, 1941 (1936)
- Helberger, Lieb. Ann. Chem., 586, 158 (1954)
- Feshin, J. Org. Chem. USSR (Engl. Transl), 12, 1052 (1976)
- Snider, J. Org. Chem., 48, 3003 (1983)
Bibliographic reference |
Schmitz, C. ; Harvey, JN. ; Viehe, HG.. Synthesis of Conjugated Dienes From Propene Or Other Alkenes By the Ene-type Reaction of Thionium Ions. In: Societes Chimiques Belges. Bulletin, Vol. 103, no. 3, p. 105-114 (1994) |
Permanent URL |
http://hdl.handle.net/2078.1/48824 |