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Synlett 1999; 1999(5): 599-601
DOI: 10.1055/s-1999-2675
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The 1-Phenylsulfonylallenyl Terminus in Intramolecular Diels-Alder Reactions: Tether Length and Reactivity

James R. Bull* , Richard S. Gordon, Roger Hunter
  • *Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa; Fax 2 72 16 50 25 46; E-mail: Bull@psipsy.uct.ac.za
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Publication Date:
31 December 1999 (online)

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Methods are described for the synthesis of 1-phenylsulfonylalka-1,2,(n + 4),(n + 6)-tetraenes 5 (n = 2-4), and preliminary findings on their thermally-induced intramolecular cycloaddition behaviour are reported. The reaction of 5 (n = 4) is slow, and engages the unactivated π-bond, whereas those of 5 (n = 2 & 3) proceed readily and exo-selectively with dienophilic participation of the activated terminal π-bond, to give the expected [4 + 2] cycloadducts. The reactivity of 5 (n = 2) is particularly noteworthy since cycloaddition proceeds under exceptionally mild conditions.

sulfonylallene - cycloaddition - allene - IMDA