Convenient and efficient synthesis of 1,1-bis-(4-alkylthiophenyl)-1-alkenes via tandem Friedel-Crafts acylation and alkylation of sulfides and acyl chlorides

Synthetic Communications

Volumn 35, Issue 17, 2005, Pages 2347-2353

  Xu, Jiaxi ^a   Xia, Jiakun ^a   Lan, Yu ^a  

^a Peking University   (China)

Author keywords

Acylation; Alkene; Alkylation; Friedel Crafts reaction; Sulfide; Tandem reaction

Indexed keywords

ALKENE DERIVATIVE; ALUMINUM CHLORIDE; SULFIDE;

ACYLATION; ALKYLATION; ARTICLE; FRIEDEL CRAFTS REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 24744453026     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910500187373     Document Type: Article

References (12)

1. For a comprehensive review of all aspects of the Friedel-Crafts reaction, see Olah, G. A. (Ed.), Friedel-Crafts and Related Reactions. Wiley-Interscience: New York, 1963-1965; Vols. 1-4.
2. Szekeres, L. A secondary reaction in the synthesis of ketones by the method of Friedel and Crafts. Gazz. Chim. Ital. 1947, 77, 465-470.
3. Mentzer, C.; Xuong, D. No. 194. Sur le mecanisme de la synthese des cetones aromatiques, selon Friedel et Crafts (Mechanism of the Friedel-Crafts synthesis of ketones). Bull. Soc. Chim. Fr. 1947, 885-892.
4. Xu, J. X.; Wei, T. Z.; Xia, J. K.; Zhang, Q. H.; Wu, H. S. Preparation of highly optically pure homochiral sulfide-containing alcohols via oxazaborolidine-catalyzed asymmetric borane reduction of ketones. Chirality 2004, 16 (6), 341-346.
5. Xu, J. X.; Su, X. B.; Zhang, Q. H. Preparation of high optically pure linear secondary alcohols via asymmetric reduction of prochiral ketones by borane. Tetrahedron: Asymmetry 2003, 14, 1781.
6. Rogig, K. 1,1-Bis-(p-methoxyphenyl)-1-propene. J. Am. Chem. Soc. 1951, 73, 865.
7. Roberts, R. M.; El-Khawaga, A. M.; Roengsumran, S. A novel Friedel-Crafts reaction of hindered ketones. J. Org. Chem. 1984, 49, 3180-3183.
8. El-Khawaga, A. M.; Roberts, R. M. Friedel-Crafts reactions of tetramethylphenyl ketones with tetramethylbenzenes. J. Org. Chem. 1984, 49, 3832-3834.
9. Schaarschmidt, A.; Hermann, L.; Szemzo, B. Aldehydes and ethylenes oxide in the Friedel-Crafts synthesis. Ber. 1925, 58B, 1914-1916.
10. Tarbell, D. S.; Lindstrom, E. G. Color reactions of some unsymmetrical diarylethylenes. J. Am. Chem. Soc. 1946, 68, 1930-1932.
11. Tadros, W.; Saad, E. Pentachlorothiophenol and some other sulfide compounds. J. Chem. Soc. 1954, 1155-1156.
12. Xuong, D.; Cagniant, P.: Mentzer, C. Synthesis of bromobis(methylmecaptophenyl)phenylethene. Compt. Rend. 1948, 226, 1453-1454.