Tetrasubstituted furans from novel [3+ 2] photocycloaddition of conjugated acetylenic α-diketones with alkenes

AK Mukherjee, WC Agosta

Index: Mukherjee, Ashis K.; Agosta, William C. Journal of the Chemical Society, Chemical Communications, 1994 , # 16 p. 1821 - 1822

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Abstract

Photocycloaddition of ketones 1a–c with tetramethylethylene 2 furnishes tetrasubstituted furans 3a–c in isolated yields of≈ 85%; a suggested mechanism for formation of 3a involves [3+ 2] cycloaddition by way of an initial biradical 5 to form an intermediate carbene 6, followed by cyclization to the furan.