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- W2950296543 abstract "Various phenylsulfonyl allene derivatives were prepared with double bonds tethered either to the α-position or the γ-position of the allene. These substrates underwent a highly regio- and stereospecific thermal [2 + 2]-cycloaddition across the nonactivated cumulene double bond, forming distal cycloadducts (i.e., 57) in the case of α-tethered allenes and proximal adducts (i.e., 25) in the case of γ-tethered allenes. The mechanistic rationale for the observed stereospecificity involves initial diradical formation, followed by a rapid ring closure to the more stable cis-fused ring system. The tether may be equipped with heteroatoms, allowing for the formation of fused heterocycles (e.g., 61), and the cycloaddition can be facilitated by the introduction of sterically bulky groups and/or by conformational rigidity to the tether. Other modes of cyclization were observed in the presence of sodium benzenesulfinate or Lewis acids, in which cases polar mechanisms prevail. The chemoselectivity is reversed for [4 + 2..." @default.
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- W2950296543 date "2003-12-09" @default.
- W2950296543 modified "2023-09-23" @default.
- W2950296543 title "Phenylsulfonyl Ene—Allenes as Efficient Precursors to Bicyclic Systems via Intramolecular [2 + 2]-Cycloaddition Reactions." @default.
- W2950296543 cites W2174061406 @default.
- W2950296543 doi "https://doi.org/10.1002/chin.200349044" @default.
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