Abstract
Reactions of organomanganese compounds RMnCl (R=3-sulfolen-2-yl or 5-methyl-3-sulfolen-2-yl) with allyl or propargyl bromides afford the corresponding 2-substituted or 2,5-disubstituted 3-sulfolenes in high yields. Thermolysis of the cross-coupling products results in 1,3,6-trienes or l,3-dien-6-ynes.
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T. Chou and H.-H. Tso,Org. Prep. Proced. Int., 1989,21, 257.
T. Chou, H.-H. Tso, and L. C. Lin,J. Org. Chem., 1986,51, 1000.
Y.-T. Tao, C.-L. Liu, and S.-J. Lee,J. Org. Chem., 1986,51, 4718.
T. Chou, H.-H. Tso, Y.-T. Tao, and L. C. Lin,J. Org. Chem., 1987,52, 244.
T. Chou, H.-H. Tso, and L.-J. Chang,J. Chem. Soc.,Chem. Commun., 1984, 1323.
T. Chou, H.-H. Tso, and L.-J. Chang,J. Chem. Soc.,Chem. Commun., 1985, 236.
T. Chou, L.-J. Chang, and H.-H. Tso,J. Chem. Soc.,Perkin Trans., I, 1986, 1039.
S. Yamada, H. Ohsawa, T. Suzuki, and H. Takayama,J. Org. Chem., 1986,51, 4934.
H. Takayama, H. Suzuki, T. Nomoto, and S. Yamada,Heterocycles, 1986,24, 303.
J. F. Normant and G. Cahiez,Modern Synthetic Methods, Ed. R. Scheffold, John Wiley & Sons, New-York, 1983,3, p. 173.
A. N. Kasatkin, O. Yu. Tsypyshev, T. Yu. Romanova, and G. A. Tolstikov,Uspekhi Khimii, 1992,61, 978 [Russ. Chem. Revs., 1992,61, 537 (Engl. Transl.)].
H. Takayama, and T. Suzuki,J. Chem. Soc., Chem. Commun., 1988, 1044.
A. N. Kasatkin, O. Yu. Tsypyshev, T. Yu. Romanova, and G. A. Tolstikov,Metalloorgan. Khimia, 1989,2, 837 [J. Organomet. Chem. USSR, 1989 (Engl. Transl.)].
A. N. Kasatkin, T. Yu. Romanova, O. Yu. Tsypyshev, and G. A. Tolstikov,Metalloorgan. Khimia, 1989,2, 470 [J. Organomet. Chem. USSR, 1989 (Engl. Transl.)].
A. N. Kasatkin, O. Yu. Tsypyshev, T. Yu. Romanova, and G. A. Tolstikov,Izv. AN SSSR, Ser. Khim., 1991, 656 (Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 573 (Engl. Transl.)].
L. V. Spirikhin, R. A. Sadykov, B. V. Flekhter, N. N. Novitskaya, A A. Panasenko, and G. A. Tolstikov,Izv. AN SSSR, Ser. Khim., 1980, 1029 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980,29, 736 (Engl. Transl.)].
O. Grummitt, A. E. Ardis, and J. Fick,J. Amer. Chem. Soc., 1950,72, 5167.
I. Ahmad, R. N. Gedye, and A. Nechvatal,J. Chem. Soc. C., 1968, 185.
J. Villieras and M. Rambaud,Synthesis, 1982, 924.
T. Chou, H.-H. Tso, and L.-J. Chang,J. Chem. Soc. Perkin Trans., I, 1985, 515.
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All = allyl.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 106–113, January, 1994.
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Kasatkin, A.N., Prokopenko, Y.A., Khabibov, A.M. et al. Cross-coupling of organomanganese derivatives of 3-sulfolenes with allyl and propargyl bromides; a simple synthesis of functionalized 1,3-dienes. Russ Chem Bull 43, 101–109 (1994). https://doi.org/10.1007/BF00699145
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DOI: https://doi.org/10.1007/BF00699145