Radical Cyclisation of o-Haloaryl Allenylmethyl Ethers and Amines: Synthesis of 3-Ethenyl-2,3-dihydrobenzofurans and 3-Ethenyl-2,3-dihydroindoles

T. Balasubramanian; K. K. Balasubramanian

doi:10.1055/s-1994-23059

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Synlett 1994; 1994(11): 946-948
DOI: 10.1055/s-1994-23059

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Radical Cyclisation of o-Haloaryl Allenylmethyl Ethers and Amines: Synthesis of 3-Ethenyl-2,3-dihydrobenzofurans and 3-Ethenyl-2,3-dihydroindoles

T. Balasubramanian^* , K. K. Balasubramanian

^*Department of Chemistry, Indian Institute of Technology, Madras 600 036, INDIA.

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Publication Date:
22 March 2002 (online)

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o-Haloaryl allenylmethyl ethers and amines upon treatment with n-Bu₃SnH and AIBN in refluxing benzene, underwent a 5-exo-trig free radical cyclisation to give the respective 3-ethenyl-2,3-dihydrobenzofurans and 3-ethenyl-2,3-dihydroindoles in good yields.