The Formation and Reaction of Carbonyl Ylide. The Copper Chelate-catalyzed Decomposition of 1-(Diazoacetyl)fluorenone in the Presence of Ethylenic and Acetylenic Compounds
作者:Toshikazu Ibata、Tadayuki Motoyama、Masashi Hamaguchi
DOI:10.1246/bcsj.49.2298
日期:1976.8
1,3-Dipolar cycloadducts were obtained by the copper chelate-catalyzed decomposition of 1-(diazoacetyl)fluorenone in the presence of acetylenic and ethylenic dipolarophiles. The reaction proceeded via intermediate carbonyl ylide (3), which has been generated by the carbene-carbonyl reaction of 2. The cycloaddition of 3 with ethylenic dipolarophiles was determined to proce d stereospecifically.
1,3-偶极环加合物是通过铜螯合物催化分解 1-(重氮乙酰基)芴酮在炔属和烯属偶极体存在下获得的。该反应通过中间体羰基叶立德 (3) 进行,该中间体是由 2 的卡宾 - 羰基反应生成的。 3 与烯键亲极体的环加成被确定为立体定向进行。