Simple and Efficient Synthesis of α-Allenic Alcohols and Their Novel Conversion into 1-Aryl-3-formyloxy-1,3-butadienes
Reactions of carbonyl compounds with 3-bromo-1-propyne in the presence of SnCl2·2H2O and LiI·3H2O gave α-allenic alcohols in moderate yields together with small amounts of β-acetylenic alcohols. The α-allenic alcohols can be converted into 1-aryl-3-formyloxy 1,3-butadienes, novel 1,3-butadiene deriv...
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| Published in | Bulletin of the Chemical Society of Japan Vol. 62; no. 10; pp. 3380 - 3382 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
The Chemical Society of Japan
01.10.1989
Chemical Society of Japan |
| Subjects | |
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| Abstract | Reactions of carbonyl compounds with 3-bromo-1-propyne in the presence of SnCl2·2H2O and LiI·3H2O gave α-allenic alcohols in moderate yields together with small amounts of β-acetylenic alcohols. The α-allenic alcohols can be converted into 1-aryl-3-formyloxy 1,3-butadienes, novel 1,3-butadiene derivatives. |
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| AbstractList | Abstract
Reactions of carbonyl compounds with 3-bromo-1-propyne in the presence of SnCl2·2H2O and LiI·3H2O gave α-allenic alcohols in moderate yields together with small amounts of β-acetylenic alcohols. The α-allenic alcohols can be converted into 1-aryl-3-formyloxy 1,3-butadienes, novel 1,3-butadiene derivatives. Reactions of carbonyl compounds with 3-bromo-1-propyne in the presence of SnCl2·2H2O and LiI·3H2O gave α-allenic alcohols in moderate yields together with small amounts of β-acetylenic alcohols. The α-allenic alcohols can be converted into 1-aryl-3-formyloxy 1,3-butadienes, novel 1,3-butadiene derivatives. |
| Author | Kanao, Yoshiaki Iyoda, Masahiko Nishizaki, Minoru Oda, Masaji |
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| Cites_doi | 10.1021/ja01304a057 10.1021/ja00233a028 10.3891/acta.chem.scand.26-2540 10.1021/ja00283a038 10.1016/S0040-4020(01)92452-4 10.1016/S0040-4020(01)91289-X |
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| Keywords | Catalytic reaction Aliphatic compound Saturated compound Bromocarbon Aldehyde Condensed benzenic compound Ketone Enol ester Bicyclic compound Conjugated dienic compound Lithium Iodides Benzenic compound Monocyclic compound |
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| References | M. Iyoda, S. Tanaka, H. Otani, M. Nose, and M. Oda, J. Am. Chem. Soc., 110, 8494 (1988). 4) P. Place, C. Verniere, and J. Gore, Tetrahedron, 37, 1359 (1981 6) H. Wollweber, “Diels-Alder Reaction,” in “Houben-Weyl, Methoden der organischen Chemie,” Georg Thieme, Stuttgart (1970), Band 5, Teil 1c, pp. 977–1139 H. Tanaka, T. Hamatani, S. Yamashita, and S. Torii, Chem. Lett., 1986, 1461. 1) M. Iyoda, M. Sakaitani, T. Miyazaki, and M. Oda, Chem. Lett., 1984, 2005 c) G. P. Boldrini, E. Tagliavini, C. Trombini, and A. Umani-Tonchi, J. Chem. Soc., Chem. Commun., 1986, 685. 5) W. H. Werntz, J. Am. Chem. Soc., 57, 204 (193 7) J. S. Cowie, P. D. Landor, and S. R. Landor, J. Chem. Soc., Perkin Trans. 1, 1973, 720. 8) A. Claesson and C. Bogentoft, Acta Chem. Scand., 26, 2540 (1972). S. D. Kahn, C. F. Pau, L. E. Overman, and W. J. Hehre, J. Am. Chem. Soc., 108, 7381 (1986). 2) D. J. Pasto, Tetrahedron, 40, 2805 (1984 M. Huche, Bull. Soc. Chim. Fr., 1975, 2369. I. N. Nazarov, G. P. Verkholetova, and L. D. Bergel’son, Chem. Abstr., 43, 2576i (1949). I. N. Nazarov, G. P. Verkholetova, and L. D. Bergel’son, Izv. Akad. Nauk SSSR, Otdel. Khim. Nauk, 1948, 511 H. F. Schuster and G. M. Coppola, “Allenes in Organic Synthesis,” John Wiley & Sons (1984) 3) a) T. Mukaiyama and T. Harada, Chem. Lett., 1981, 621 b) J. Nokami, T. Tamaoka, T. Koguchi, and R. Okawara, Chem. Lett., 1984, 1939 2024011815000143000_r9 2024011815000143000_r7 2024011815000143000_r8 2024011815000143000_r5 2024011815000143000_r6 2024011815000143000_r3 2024011815000143000_r17 2024011815000143000_r4 2024011815000143000_r16 2024011815000143000_r1 2024011815000143000_r15 2024011815000143000_r2 2024011815000143000_r14 2024011815000143000_r13 2024011815000143000_r12 2024011815000143000_r11 2024011815000143000_r10 |
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| Snippet | Reactions of carbonyl compounds with 3-bromo-1-propyne in the presence of SnCl2·2H2O and LiI·3H2O gave α-allenic alcohols in moderate yields together with... Abstract Reactions of carbonyl compounds with 3-bromo-1-propyne in the presence of SnCl2·2H2O and LiI·3H2O gave α-allenic alcohols in moderate yields together... |
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| Title | Simple and Efficient Synthesis of α-Allenic Alcohols and Their Novel Conversion into 1-Aryl-3-formyloxy-1,3-butadienes |
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