Ring-closing reaction of allenic/propargylic anions generated by base treatment of sulfonylallenes.
Ring-closing reaction of allenic/propargylic anions generated by base treatment of sulfonylallenes.
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DOI：
10.1002/chin.200743029
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发表时间：
2007-05
期刊：
影响因子：
5.2
通讯作者：
S. Kitagaki;S. Teramoto;C. Mukai
中科院分区：
文献类型：
--
作者：
S. Kitagaki;S. Teramoto;C. Mukai
研究了磺基联苯类化合物碱处理产生的烯丙基/炔丙基阴离子的分子内捕获行为。在DMF中，1-(欧米伽-碘烷基)-1-(苯磺酰基)-1-烯与TBAF或NaH反应可有效地生成三至七元的1-乙炔基-1-(苯磺酰基)取代碳环。烯丙基/炔丙基阴离子也可以用端醛或α，β-不饱和酯分子内捕获。在这一新的闭环反应中，苯磺酰基被其他吸电子官能团如酮和酯基取代，但没有被烷基取代。
The intramolecular trapping of allenyl/propargyl anions generated by base treatment of sulfonylallenes was investigated. Treatment of 1-(omega-iodoalkyl)-1-(phenylsulfonyl)allenes with TBAF or NaH in DMF efficiently produced three- to seven-membered 1-ethynyl-1-(phenylsulfonyl) substituted carbocycles. The allenyl/propargyl anions could also be intramolecularly trapped using a terminal aldehyde or alpha,beta-unsaturated ester. The phenylsulfonyl group was found to be replaced by other electron-withdrawing functionalities like ketone and ester groups but not by an alkyl group for this novel ring-closing reaction.