醛酮和LiTMSD（三甲基硅基重氮甲烷鋰鹽）反應后，接著消除（Peterson烯合成 ）脫氮氣得到卡賓，重排生成多一個碳的炔烴的反應。反應中的卡賓重排類似Fritsch–Buttenberg–Wiechell重排反應。
環酮可以通過此反應擴環得到多一個碳的環炔類化合物。
反應機理
反應實例
p-Methoxyphenylpropyne (4). To LDA in THF (8 mL) was added trimethylsilyldiazomethane 2 (1.9 M in hexane, 0.63 mL, 1.2 mmol) at -78 C under Ar. After 30 min, ketone 1 (150 mg, 1 mmol) in THF (2 mL) was added dropwise at 78 C. After 1 h the mixture was refluxed for 3 h, quenched
(H2O) and extracted with Et2O. Evaporation and chromatography provided 199.7 mg of 4 (82%), bp 85–88 C/0.9 mm.
【Aoyama T, Shiori T, Tet Lett, 1994, 35, 107】
相關文獻
1 Colvin EV J Chem Soc Chem Comm 1973 151
2 Colvin EV J Chem Soc Perkin Trans 1 1977 869
3 Colvin EV J Chem Soc Chem Comm 1992 721
4 Aoyama T, Shiori T Tet Lett 1994 35 107
5 Roth GJ Synthesis 2004 59
6 Mulzer J Angew Chem Int 2009 48 6032
編譯自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 93.
