Synthesis and acid-catalyzed ring opening of 1-alkenyl cyclopropyl ketones

O Tsuge, S Kanemasa, T Otsuka, T Suzuki

文献索引：Tsuge, Otohiko; Kanemasa, Shuji; Otsuka, Tatsuya; Suzuki, Toshiro Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 2897 - 2908

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被引用次数: 32

摘要

1-Alkenyl cyclopropyl ketones, when activated by cation-stabilizing substituents at the ring carbon or at the terminal carbon of the enone moiety, undergo polyphosphoric acid- catalyzed ring enlargement producing cyclopentanone or cyclohexenone derivatives. Similar acid-catalyzed ring opening of 1-alkenyl 2-phenoxycyclopropyl ketones offers a convenient and effective synthesis of 4-oxo-5-alkenals and their dioxolaneprotected ...