著者

村上 正志 西田 進也

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.41, no.1, pp.22-37, 1983-01-01 (Released:2010-04-23)

参考文献数

137

被引用文献数

11 12

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Chemical characteristics of cyclopropyl derivatives are classified and organic syntheses with practical utilization of these characteristics are reviewed. The classification involves : (1) additions of X-Y to a strained cyclopropyl sigma bond with ring cleavage; (2) additions of a nucleophile to activated cyclopropyl derivatives; (3) isomerizations of cyclopropyl cations, anions, and radicals to allylic species; (4) isomerizations of cyclopropylmethyl cations, anions, and radicals to either cyclobutyl or 3-butenyl species; (5) allenes from cyclopropylidenes and cyclopentadienes from 2-vinylcyclopropylidenes; (6) rearrangement of cyclopropylcarbenes to cyclobutenes; (7) reactions involving homolytic cleavage of a cyclopropane sigma bond; (8) vinylcyclopropane-cyclopentene rearrangement; (9) cis-1, 2-divinylcyclopropane-cyclohepta-1, 4-diene rearrangement and homo-1, 5-hydrogen migration; (10) homolyses of cyclopropene yielding vinylcarbenes ; (11) cycloadditions of some specifically activated olefins to cyclopropane derivatives; and (12) reactions of cyclopropene derivatives followed by ring cleavage of the resultant three-membered ring compounds.