A stereoselective synthesis of 1,2-dialkylethenyl bromides via monohydroboration of 1-bromo-1-alkynes with dialkylboranes.
作者： Yuzuru Masuda , Akira Arase , Akira Suzuki
DOI: 10.1246/CL.1978.665
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摘要: Treatment of 1-bromo-1-alkenyldialkylboranes with lead(IV) acetate or iodosobenzene diacetate afforded 1-bromo-1,2-dialkylethylenes in moderate yields. Furthermore, both E-isomers and Z-isomers could be independently obtained as the main products by use different reaction conditions.
csj.jp参考文章(7)
G. Zweifel, R. P. Fisher, J. T. Snow, C. C. Whitney, Stereoselective introduction of olefinic side chains onto cyclic systems via the hydroboration-iodination of alkynes Journal of the American Chemical Society. ,vol. 93, pp. 6309- 6311 ,(1971) , 10.1021/JA00752A075
Herbert Charles Brown, Shyam Kirti Gupta, New addition compounds of dialkylboranes and aluminum methoxide. New practical synthesis of dialkylboranes and of mixed trialkylboranes containing functional groups Journal of the American Chemical Society. ,vol. 93, pp. 1818- 1819 ,(1971) , 10.1021/JA00736A062
Yuzuru Masuda, Akira Arase, The Formation of Alkyl Acetate in the Reaction of Trialkylborane with Lead(IV) Acetate or Phenyliodoso Acetate Bulletin of the Chemical Society of Japan. ,vol. 51, pp. 901- 904 ,(1978) , 10.1246/BCSJ.51.901
K.-E. Schulte, M. Goes, Die Darstellung von Alkin‐aminen Archiv Der Pharmazie. ,vol. 290, pp. 118- 130 ,(1957) , 10.1002/ARDP.19572900303
Herbert Charles. Brown, Donald H. Bowman, Soichi. Misumi, M. K. Unni, Synthesis of both cis- and trans-vinyl bromides from 1-alkynes via hydroboration Journal of the American Chemical Society. ,vol. 89, pp. 4531- 4532 ,(1967) , 10.1021/JA00993A055
Herbert C. Brown, Akira Tsukamoto, D. B. Bigley, Hydroboration. VI. A Convenient Synthesis of the Alkane and Cycloalkane Boronic and Borinic Esters and Acids Journal of the American Chemical Society. ,vol. 82, pp. 4703- 4707 ,(1960) , 10.1021/JA01502A062
George. Zweifel, Henri. Arzoumanian, Charles C. Whitney, A convenient stereoselective synthesis of substituted alkenes via hydroboration-iodination of alkynes Journal of the American Chemical Society. ,vol. 89, pp. 3652- 3653 ,(1967) , 10.1021/JA00990A061