Fujita Morifumi, Oshima Makoto, Okuno Sakuro, Sugimura Takashi, Okuyama Tadashi
Graduate School of Material Science, Himeji Institute of Technology, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan.
Org Lett. 2006 Aug 31;8(18):4113-6. doi: 10.1021/ol061655t.
The ring opening of alkylidenecyclopropanone acetal under acidic conditions produces the 1-alkylidene-2-oxyallyl cation as an intermediate, which reacts with furan to give the [3 + 2] and [4 + 3] cycloadducts as well as an electrophilic substitution product. The product distribution is controlled by the oxy substituents of the cation and by the solvent employed.
亚烷基环丙烷酮缩醛在酸性条件下开环会生成1-亚烷基-2-氧代烯丙基阳离子中间体,该中间体与呋喃反应生成[3 + 2]和[4 + 3]环加成产物以及一种亲电取代产物。产物分布受阳离子的氧取代基和所用溶剂的控制。