Influence of Ring Strain on the Formation of Rearrangement vs Cyclization Isotwistane Products in the Acyl Radical Reaction of Bicyclo[2.2.2]octanone

Chih Ming Chen, Sheng Kuo Lin, Chi Tien Hsieh, Julakanti Satyanarayana Reddy, Yi Ning Teoh, Mu Jeng Cheng, Hsing-Pang Hsieh

研究成果: Article同行評審

摘要

An acyl radical reaction of bicyclo[2.2.2]octenone to yield either rearranged or cyclized isotwistane products is described. The influence of ring strain on the reaction was demonstrated by alternating the sizes of the fused ring in the starting material. DFT calculations showed that the reaction is under thermodynamic control and proceeds via a 5-exo-trig cyclization intermediate, which undergoes either hydrogen-atom transfer (HAT) to give a cyclized product or rearrangement via a twistane intermediate to give a rearranged product.

原文English
頁(從 - 到)7757-7762
頁數6
期刊Organic Letters
25
發行號43
DOIs
出版狀態Published - 2023 11月 3

All Science Journal Classification (ASJC) codes

  • 生物化學
  • 物理與理論化學
  • 有機化學

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