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Synlett 1995; 1995(8): 866-868
DOI: 10.1055/s-1995-5090
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A Facile Method for Preparation of Functionalized Cyclopropene Derivatives. Synthesis of Cyclopropene-Related Allylic and Homoallylic Alcohols

Pawel Jankowski, Marek Masnyk, Jerzy Wicha*
  • *Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, 01-224 Warsaw, Poland
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Publication Date:
31 December 2000 (online)

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Free-radical addition of iodoalkyl sulphones 1 to vinylsilanes 2 afforded adducts 3 regioselectively. The adducts were cyclized to give cyclopropanes 4 and then transformed into the cyclopropene derivatives 5. Addition of iodomethyl phenyl sulphone (6) to triphenylvinylsilane 7 followed by cyclization of the adduct provided cyclopropane 8. The latter was reacted with representative alkylating agents to afford the corresponding products 11 and 12. Alcohol 12a was transformed into cyclopropene-related allylic alcohol 14b.

α-iodoalkyl sulphones - free-radical addition - iodosulphone cyclization - cyclopropanes - cyclopropenes

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