Hofmann异腈合成反应
伯胺在碱性条件下和二卤卡宾反应得到异腈。常用的碱是季铵碱。二卤卡宾通过氯仿或溴仿在碱性条件下得到直接用于反应。
反应机理
反应实例
Phenylisocyanide (3). To PhNH2 1 (18.6 g, 0.2 mol), alcohol free 2 (24 g, 0.2 mol) and benzyltrimethyl ammonium chloride (0.5 g) in DCM (60 mL) was added at once 50% NaOH (60 mL). After 10 min induction, reflux began. Reflux and stirring for 1 h and workup gave 12 g of 3 (57%), bp 50–52 C/11 Torr.
【Weber WP, Tet Lett., 1972, 1637】
相关文献
1 Hofmann AW Liebig’s Ann 1868 146 107
2 Smith PAS J Org Chem 1958 23 1599
3 Ugi JK Angew Chem Int 1972 11 530
4 Weber WP Tet Lett 1972 1637
5 Weber WP Org Synth Coll 1988 6 232
6 Pirrung MC J Am Chem Soc 2006 128 11772
编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 223.
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