A Novel Synthesis of 2,5,8,11-Tetrahydro-1,7-dioxabenzo[1,2,4,5]dicycloheptene from Hydroquinone via Claisen Rearrangement and Ring-closing Metathesis Reaction

碩士 === 國立高雄醫學大學 === 藥學研究所碩士在職專班 === 90 === In this study, the diallyl phenyl ether, 1,4-diallyloxybenzene (2), was synthesized from hydroquinone (1) with allyl bromide. 1,4-di- allyloxybenzene (2) was performed the Claisen rearrangement to obtain di-O-allyl phenols, 2,5-diallylhydroquinone (3)....

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Bibliographic Details
Main Authors: Lin-Hui Kuo, 郭玲惠
Other Authors: Eng-Chi Wang
Format: Others
Language:zh-TW
Published: 2002
Online Access:http://ndltd.ncl.edu.tw/handle/09894368990548647868
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Summary:碩士 === 國立高雄醫學大學 === 藥學研究所碩士在職專班 === 90 === In this study, the diallyl phenyl ether, 1,4-diallyloxybenzene (2), was synthesized from hydroquinone (1) with allyl bromide. 1,4-di- allyloxybenzene (2) was performed the Claisen rearrangement to obtain di-O-allyl phenols, 2,5-diallylhydroquinone (3). Furthermore, compound 3 was performed the allylation again with allyl bromide to give 2,5-diallyl-1,4-diallyloxybenzene (4). Then, 2,5-diallyl-1,4-diallyloxybenzene (4) used the Grubbs catalysts to undergo the ring-closing metathesis reaction, and furnished a novel 7-6-7 tricyclic compound, 2,5,8,11-tetrahydro-1,7-dioxabenzo[1,2,4,5]dicyclo- heptene (5).