杏耀几年

将伯胺转化为异腈，接着通过自由基反应脱除异腈得到相应脱胺基产物的反应。此反应也被称为 –Saegusa反应。异硫氰化物（isothionitriles）和异硒氰化物（isoselenonitriles）也可进行相似的反应。当异腈基团连接到叔碳上时，反应更加容易进行。

反应机理

机理与Barton-McCombie脱羟基反应类似

反应实例

Octadecane (4). A solution of 3 (0.279 g, 1 mmol) and AIBN (0.1 g) in dry xylene (50 mL) was added dropwise to a solution of tri-n-butyl stannane (0.64 g, 2.2 mol equiv). A solution of AIBN (0.1 g) in xylene (50 mL) was slowly added at 80 C over 5 h. The solvent was removed in vacuum, the residue dissolved in pentane and iodine in pentane was added until the iodine color persisted.

The solvent was evaporated and 4 was isolated by preparative TLC (silica gel, pentane). Sublimation in vacuum gave 0.205 g of 4 (81%), mp 29 C.

【Saegusa T， J Am Chem Soc， 1968， 90， 4182】

【 Baran PS, J Am Chem Soc, 2009, 131, 17066】

相关文献

1 Saegusa T J Am Chem Soc 1968 90 4182

2 Barton DHR Tet Lett 1979 2291

3 Barton DHR J Chem Soc Perkin 1 1980 2657

4 Swindell CS J Org Chem 1990 55 3

5R Barton DHR Aldrichim Acta 1990 23 3

6 Baran PS J Am Chem Soc 2009 131 17066

编译自：Organic Syntheses Based On , 3RdEd, A. Hassner, Page 33-34.

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