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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。

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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co1,5-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。


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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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