Samarium(II) Iodide-Promoted Reactions of 2,3-Epoxycycloalkanone Hydrazones

Han-Young Kang; Woo Sang Hong; Sang Hak Lee; Kyung Il Choi; Hun Yeong Koh

doi:10.1055/s-1997-713

Synlett 1997; 1997(1): 33-34
DOI: 10.1055/s-1997-713

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Samarium(II) Iodide-Promoted Reactions of 2,3-Epoxycycloalkanone Hydrazones

Han-Young Kang¹ , Woo Sang Hong¹ , Sang Hak Lee¹ , Kyung Il Choi² , Hun Yeong Koh²

¹Department of Chemistry, Chungbuk National University, Cheongju, Chungbuk 361-763, Korea
²Division of Applied Science, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea

Abstract

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The reaction of hydrazones of 2,3-epoxycycloalkanone promoted by samarium(II) iodide has been investigated to study the behavior of the compounds containing C=N bonds in the presence of this powerful single-electron transfer reagent. For the hydrazones derived from 2,3-epoxycyclopentanone and 2,3-epoxycyclohexanone, 3-iodo-2-cycloalkenols were isolated while the corresponding 2-cycloalkenols were the products when the hydrazones from 2,3-epoxycycloheptanone and 2,3-epoxycyclooctanone were reacted.

Samarium(II) iodide - hydrazones - epoxycycloalkanone - C=N bonds - iodination

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