Ring-Closure Reactions. 13.¹ A Convenient Synthesis of Many-Membered Thiacycloalkanes

References

• Galli , C. , Giovannelli , G. , Illuminati , G. and Mandolini , L. 1979 . J. Org. Chem. , 44 : 1258 Part
   Google Scholar
• Farmaceutická Fakulta University Karlovy, 500 27 Hradec Králové, Czechoslovakia
   Google Scholar
• Friedman , P. and Allen , P. Jr. 1962 . J. Org. Chem. , 27 : 1095
   Web of Science ®Google Scholar
• Friedman , P. and Allen , P. Jr. 1965 . J. Org. Chem. , 30 : 780
   Web of Science ®Google Scholar
• Müller , A. and Schütz , A. F. 1938 . Ber. , 71 : 692
   Google Scholar
• Müller , A. , Funder-Fritzsche , E. , Konar , W. and Rintersbacker-Wlasak , E. 1953 . Monatsh. , 84 : 1206
   Google Scholar
• Illuminati , G. , Mandolini , L. and Masci , B. 1974 . J. Org. Chem. , 39 : 2598 C. Galli and L. Mandolini, Gazz. Chim. Ital., 105, 367(1975); L. Mandolini and B. Masci, J. Org. Chem., 42, 2840(1977)
   Web of Science ®Google Scholar
• Dibromoalkanes up to C12 were commercial samples. 1,14-Dibromotetradecane was prepared as follows. Treatment of 1,12-dibromododecane with two molar equivalents of sodium diethyl malonate, followed by hydrolysis and decarboxylation gave hexadecanedioic acid in 64% overall yield, mp 123–124 oC, lit, 9 mp 123–124 oC. The dicarboxylic acid was converted into 1,14-dibromotetradecane in 83% yield according to the Cason and Welba's modification10 of the Hunsdiecker reaction. The product, purified by chromatography on silica gel with CHC13/light petroleum 1:9, had mp 46–47 oC, lit, 11 47.5–48 oC
   Google Scholar
• Chuit , P. 1926 . Helv. Chim. Acta , 9 : 274
   Google Scholar
• Cason , J. and Welba , D. H. 1972 . J. Org. Chem. , 37 : 669
   Google Scholar
• Woolford , R. G. 1962 . Can. J. Chem. , 40 : 1846
   Google Scholar