Barton反应在1960年首次报道亚硝酸酯在光照下生成δ-亚硝基的醇,并可进一步衍生成δ-羟基的肟。
反应机理
该反应为自由基机理。首先在光照下,RO-NO键发生异裂生成氧自由基和氮氧自由基,接着自由基发生从C到O的1,5-氢迁移,生成碳自由基。碳自由基和氮氧自由基结合生成最终产物。
参考文献
1. Barton, D. H. R., Beaton, J. M., Geller, L. E., Pechet, M. M. J. Am.Chem. Soc. 1960, 82, 2640-2641.
2. Barton, D. H. R., Beaton, J. M., Geller, L. E., Pechet, M. M. J. Am.Chem. Soc. 1961, 83, 4076-4083.
3. Nussbaum, A. L., Yuan, E. P., Robinson, C., Mitchell, A., Oliveto,E. P., Beaton, J. M., Barton, D. R. J. Org. Chem. 1962, 27, 20-23.
4. Corey, E. J., Arnett, J. F., Widiger, G. N. J. Am. Chem. Soc. 1975,97, 430-431.
5. Sejbal, J., Klinot, J., Vystrcil, A. Collect. Czech. Chem. Commun.1988, 53, 118-131.
6. Petrovic, G., Cekovic, Z. Tetrahedron Lett. 1997, 38, 627-630.
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