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Optional Synthesis of 2- or 5-Substituted 3-Bromopyrroles via Bromine-Lithium Exchange of N-Benzenesulfonyl-2,4-dibromopyrrole
http://hdl.handle.net/10069/33701
http://hdl.handle.net/10069/33701ae9908b6-7d49-46ae-a774-69b598c8f10d
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supporting info.pdf (533.4 kB)
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Het86_1261.pdf (884.2 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2013-09-18 | |||||
タイトル | ||||||
タイトル | Optional Synthesis of 2- or 5-Substituted 3-Bromopyrroles via Bromine-Lithium Exchange of N-Benzenesulfonyl-2,4-dibromopyrrole | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Fukuda, Tsutomu
× Fukuda, Tsutomu× Iwao, Masatomo |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | The regioselective bromine–lithium exchange of N-benzenesulfonyl-2,4-dibromopyrrole (6) with n-BuLi followed by treatment with various electrophiles gave 5-substituted 3-bromopyrroles (5) in excellent yields. In contrast, the sequential treatment of 6 with n-BuLi and diisopropylamine followed by quenching with electrophiles produced regioisomeric 2-substituted 3-bromopyrroles (3) selectively. The latter reaction can be rationalized by the rapid equilibration of the C-5 lithio species (4) to the more stable C-2 lithio species (2) in the presence of diisopropylamine. | |||||
書誌情報 |
HETEROCYCLES 巻 86, 号 2, p. 1261-1273, 発行日 2012-08-21 |
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出版者 | ||||||
出版者 | 日本複素環化学研究所 | |||||
出版者別言語 | ||||||
Japan Institute of Heterocyclic Chemistry | ||||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 03855414 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.3987/COM-12-S(N)81 | |||||
権利 | ||||||
権利情報 | © 2012 The Japan Institute of Heterocyclic Chemistry | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | HETEROCYCLES, 86(2), pp.1261-1273; 2012 |