AI Article Synopsis

  • Iodobenzene diacetate facilitates reactions between methylenecyclopropanes, vinylidenecyclopropanes, and methylenecyclobutanes with phthalhydrazide, resulting in [3+2] cycloaddition products.
  • The transformation of phthalhydrazide involves its conversion into a 1,3-dipole intermediate thanks to the action of iodobenzene diacetate.
  • A potential reaction mechanism for these processes has been suggested.

Article Abstract

[structure: see text]. Iodobenzene diacetate-mediated reactions of methylenecyclopropanes 1, vinylidenecyclopropanes 2, and a methylenecyclobutane 3a with phthalhydrazide give the corresponding [3+2] cycloaddition products in good yields under mild conditions. In these reactions, phthalhydrazide was transformed to a 1,3-dipole intermediate in the presence of iodobenzene diacetate. A plausible reaction mechanism has been proposed.

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http://dx.doi.org/10.1021/ol070178rDOI Listing

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