Talk:N-溴代丁二酰亚胺

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message: N-Bromosuccinimide or NBS is a chemical reagent which is used in radical substitution and electrophilic addition reactions in organic chemistry. NBS can be considered a convenient source of bromine.
thread_title: 从英文版翻译

message: ===Addition to alkenes===
NBS will react with alkenes 1 in aqueous solvents to give bromohydrins 2. The preferred conditions are the portionwise addition of NBS to a solution of the alkene in 50% aqueous DMSO, DME, THF, or tert-butanol at 0°C.Hanzlik, R. P. Organic Syntheses, Coll. Vol. 6, p.560 (1988); Vol. 56, p.112 (1977). (Article) Formation of a bromonium ion and immediate attack by water gives strong Markovnikov addition and anti stereochemical selectivities.Beger, J. J. Prakt. Chem. 1991, 333(5), 677-698.
Side reactions include the formation of α-bromo-ketones and dibromo compounds. These can be minimized by the use of freshly recrystallized NBS.
With the addition of nucleophiles, instead of water, various bifunctional alkanes can be synthesized.Haufe, G.; Alvernhe, G.; Laurent, A.; Ernet, T.; Goj, O.; Kröger, S.; Sattler, A. Organic Syntheses, Coll. Vol. 10, p.128 (2004); Vol. 76, p.159 (1999). (Article)
===Allylic and benzylic bromination===
Standard conditions for using NBS in allylic and/or benzylic bromination involves refluxing a solution of NBS in anhydrous CCl4 with a radical initiator, usually azo-bis-isobutyronitrile (AIBN), benzoyl peroxide, irradiation, or both to effect radical initiation.Djerassi, C.; Chem. Rev. 1948, 43, 271.Greenwood, F. L.; Kellert, M. D.; Sedlak, J. Organic Syntheses, Coll. Vol. 4, p.108 (1963); Vol. 38, p.8 (1958). (Article) This is also called the Wohl-Ziegler reaction.Wohl, A. Ber. 1919, 52, 51.Ziegler, K.; et al. Ann. 1942, 551, 30.
The carbon tetrachloride must be maintained anhydrous throughout the reaction, as the presence of water may likely hydrolyze the desired product.Binkley, R. W.; Goewey, G. S.; Johnston, J; J. Org. Chem. 1984, 49, 992. Barium carbonate is often added to maintain anhydrous and acid-free conditions.
===Bromination of carbonyl derivatives===
NBS can α-brominate carbonyl derivatives via either a radical pathway (as above) or via acid-catalysis. For example, hexanoyl chloride 1 can be brominated in the alpha-position by NBS using acid catalysis.Harpp, D. N.; Bao, L. Q.; Coyle, C.; Gleason, J. G.; Horovitch, S. Organic Syntheses, Coll. Vol. 6, p.190 (1988); Vol. 55, p.27 (1976). (Article)
The reaction of enolates, enol ethers, or enol acetates with NBS is the preferred method of α-bromination as it is high-yielding with few side-products.Stotter, P. L.; Hill, K. A.; J. Org. Chem. 1973, 38, 2576.Lichtenthaler, F. W.; et al. Synthesis 1992, 179.
===Bromination of aromatic derivatives===
Electron-rich aromatic compounds, such as phenols, anilines, and various aromatic heterocyclesAmat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. Organic Syntheses, Coll. Vol. 9, p.417 (1998); Vol. 74, p.248 (1997). (Article), can be brominated using NBS.Gilow, H. W.; Burton, D. E.; J. Org. Chem. 1981, 46, 2221.Brown. W. D.; Gouliaev, A. H. Organic Syntheses, Vol. 81, p.98 (2005). (Article) Using DMF as the solvent gives high levels of para-selectivity.Mitchell, R. H.; Lai, Y.-H.; Williams, R. V.; J. Org. Chem. 1979, 44, 4733.
===Hofmann rearrangement===
NBS, in the presence of a strong base, such as DBU, reacts with primary amides to produce a carbamate via the Hofmann rearrangement.Keillor, J. W.; Huang, X. Organic Syntheses, Coll. Vol. 10, p.549 (2004); Vol. 78, p.234 (2002). (Article)
===Selective oxidation of alcohols===
It is uncommon, but possible for NBS to oxidize alcohols. E. J. Corey et al. found that one can selectively oxidize secondary alcohols in the presence of primary alcohols using NBS in aqueous DME.Corey, E. J.; Ishiguro, M. Tetrahedron Lett. 1979, 20, 2745-2748.
thread_title:  Chemistry 

message: NBS will react with alkenes 1 in aqueous solvents to give bromohydrins 2. The preferred conditions are the portionwise addition of NBS to a solution of the alkene in 50% aqueous DMSO, DME, THF, or tert-butanol at 0°C.Hanzlik, R. P. Organic Syntheses, Coll. Vol. 6, p.560 (1988); Vol. 56, p.112 (1977). (Article) Formation of a bromonium ion and immediate attack by water gives strong Markovnikov addition and anti stereochemical selectivities.Beger, J. J. Prakt. Chem. 1991, 333(5), 677-698.
Side reactions include the formation of α-bromo-ketones and dibromo compounds. These can be minimized by the use of freshly recrystallized NBS.
With the addition of nucleophiles, instead of water, various bifunctional alkanes can be synthesized.Haufe, G.; Alvernhe, G.; Laurent, A.; Ernet, T.; Goj, O.; Kröger, S.; Sattler, A. Organic Syntheses, Coll. Vol. 10, p.128 (2004); Vol. 76, p.159 (1999). (Article)
thread_title: Addition to alkenes

message: Standard conditions for using NBS in allylic and/or benzylic bromination involves refluxing a solution of NBS in anhydrous CCl4 with a radical initiator, usually azo-bis-isobutyronitrile (AIBN), benzoyl peroxide, irradiation, or both to effect radical initiation.Djerassi, C.; Chem. Rev. 1948, 43, 271.Greenwood, F. L.; Kellert, M. D.; Sedlak, J. Organic Syntheses, Coll. Vol. 4, p.108 (1963); Vol. 38, p.8 (1958). (Article) This is also called the Wohl-Ziegler reaction.Wohl, A. Ber. 1919, 52, 51.Ziegler, K.; et al. Ann. 1942, 551, 30.
The carbon tetrachloride must be maintained anhydrous throughout the reaction, as the presence of water may likely hydrolyze the desired product.Binkley, R. W.; Goewey, G. S.; Johnston, J; J. Org. Chem. 1984, 49, 992. Barium carbonate is often added to maintain anhydrous and acid-free conditions.
thread_title: Allylic and benzylic bromination

message: NBS can α-brominate carbonyl derivatives via either a radical pathway (as above) or via acid-catalysis. For example, hexanoyl chloride 1 can be brominated in the alpha-position by NBS using acid catalysis.Harpp, D. N.; Bao, L. Q.; Coyle, C.; Gleason, J. G.; Horovitch, S. Organic Syntheses, Coll. Vol. 6, p.190 (1988); Vol. 55, p.27 (1976). (Article)
The reaction of enolates, enol ethers, or enol acetates with NBS is the preferred method of α-bromination as it is high-yielding with few side-products.Stotter, P. L.; Hill, K. A.; J. Org. Chem. 1973, 38, 2576.Lichtenthaler, F. W.; et al. Synthesis 1992, 179.
thread_title: Bromination of carbonyl derivatives

message: Electron-rich aromatic compounds, such as phenols, anilines, and various aromatic heterocyclesAmat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. Organic Syntheses, Coll. Vol. 9, p.417 (1998); Vol. 74, p.248 (1997). (Article), can be brominated using NBS.Gilow, H. W.; Burton, D. E.; J. Org. Chem. 1981, 46, 2221.Brown. W. D.; Gouliaev, A. H. Organic Syntheses, Vol. 81, p.98 (2005). (Article) Using DMF as the solvent gives high levels of para-selectivity.Mitchell, R. H.; Lai, Y.-H.; Williams, R. V.; J. Org. Chem. 1979, 44, 4733.
thread_title: Bromination of aromatic derivatives

message: NBS, in the presence of a strong base, such as DBU, reacts with primary amides to produce a carbamate via the Hofmann rearrangement.Keillor, J. W.; Huang, X. Organic Syntheses, Coll. Vol. 10, p.549 (2004); Vol. 78, p.234 (2002). (Article)
thread_title: Hofmann rearrangement

message: It is uncommon, but possible for NBS to oxidize alcohols. E. J. Corey et al. found that one can selectively oxidize secondary alcohols in the presence of primary alcohols using NBS in aqueous DME.Corey, E. J.; Ishiguro, M. Tetrahedron Lett. 1979, 20, 2745-2748.
thread_title: Selective oxidation of alcohols

message: NBS is commercially available. It can also be synthesized in the laboratory. To do so, sodium hydroxide and bromine are added to an ice-water solution of succinimide. The NBS product precipitates out and can be collected by filtration.
Crude NBS gives better yield in the Wohl-Ziegler reaction. In other cases, impure NBS (slightly yellow-colored) may give unreliable results. It can be purified by recrystallization from 90-95 °C water.
thread_title: Preparation

message: Although NBS is easier and safer to handle than bromine, precautions should be taken to avoid inhalation. NBS should be stored in a refrigerator. NBS will decompose over time giving off bromine. Pure NBS is white, but it is often found to be off-white or brown colored by bromine.
In general, reactions involving NBS are exothermic. Therefore, extra precautions should be taken when used on a large scale.
thread_title: Precautions

message: *Halohydrin formation
thread_title: See also

thread_title: References

message: * N-bromosuccinimide External MSDS
* Usage of N-Bromosuccinimide in Organic Syntheses
{{DEFAULTSORT:Bromosuccinimide, N-}}
[[:Category:Organobromides]]
[[:Category:Reagents for organic chemistry]]
[[:de:N-Bromsuccinimid]]
[[:ja:N-ブロモスクシンイミド]]
[[:pl:NBS]]
-Zhuhui 2007年8月1日 (三) 19:43 (UTC)
thread_title: External links

message: 各位可参考WP:DYKC候选区的意见进行改善。--食人魔国王Talk 2015年7月9日 (四) 02:39 (UTC)
replies: text: 第一點所述內容已刪除，第三點及之後各點已經改善。第二點留待原作者處理。--William915（与我讨论） 2015年7月9日 (四) 13:27 (UTC)
replies: text: :不好意思這麼晚才回覆您，感謝您再次為我的不專業翻譯抓出錯誤
replies: text: ::1.這部分我太粗心了，寫的時候竟然把整段文字給遺漏了，已補上。

text: ::2.的確文獻上沒有註明溫度，經過搜尋之後也沒有找到相關資料，所以刪除。

text: ::3.我來試試看能不能直接改圖

text: ::謝謝您幫我改正第4條之後的問題。原來在有文獻支持的狀況下還有這麼多不準確！之後做翻譯的時候我會多多注意的，還請多多指教了。

text: ::（PS. 根據使用者:和平奮鬥救地球/自然科學條目提升計劃的統計，雖然化學類的條目在維基的自然科條目中相對算是不缺乏的，但許多最基本的條目內容還是相當不足，還請您有空的話多多關注他們，最近發現我這種非化學本科專業的學生寫起條目來還是有極限的，許多條目好像看得懂卻都不敢碰><″）--Yrr933!(留言) 2015年7月10日 (五) 07:42 (UTC)
**：條目翻譯自英文維基，擴充約8400位元組--Yrr933!(留言) 2015年7月5日 (日) 08:33 (UTC)
**：符合标准，部分错字与N的斜体显示问题已作修改。--William915（与我讨论） 2015年7月5日 (日) 08:56 (UTC)
**：符合标准。--V  (1984) 2015年7月5日 (日) 08:48 (UTC)
**：符合标准。--Walter Grassroot (♬) 2015年7月6日 (一) 13:01 (UTC)
**：符合标准。4Li 2015年7月7日 (二) 01:42 (UTC)
**，符合標準。--Iflwlou [ M {  2015年7月7日 (二) 07:14 (UTC)
***
#你告诉我，“將0.16莫耳（約16 g）的丁二醯亞胺溶於至於冰浴中的氫氧化鈉溶液中（6.4 g溶入40 mL水中並加入30 g碎冰），持續攪拌約5分鐘後，過濾並以清水清洗產物”的过程中有没有发生核反应？溴从哪里来？--Antigng（留言） 2015年7月7日 (二) 08:05 (UTC)
#来源4中何处提到“進行此反應的最佳條件是在0 °C下，將NBS分批加入烯烴的DMSO或DME或THF或叔丁醇其中之一的50 %水溶液中。”--Antigng（留言） 2015年7月7日 (二) 08:17 (UTC)
#右图有错，反应产物应当是消旋的。
#“進行烯丙基類與苯甲基類化合物的溴化反應的基本條件是在迴流裝置中將NBS溶入無水四氯化碳。”溶吗？9号、10号注释失效，无法查证。--Antigng（留言） 2015年7月7日 (二) 08:22 (UTC)
#“然而為了使此反應有較高的產率和較少其他副產物產生，通常會使用NBS加上烯醇或烯醇醚，這樣也能產生α-溴化反應。”脚注13明明是烯醇锂盐的溴化反应，怎么在条目里写成了烯醇与NBS德反应？有多少烯醇可以稳定存在？--Antigng（留言） 2015年7月7日 (二) 08:30 (UTC)
#“擁有高電子密度的芳香類化合物像是酚、苯胺或雜環化合物……”杂环化合物都具有高电子密度？你可以试试用NBS给吡啶溴化。--Antigng（留言） 2015年7月7日 (二) 08:33 (UTC)
#“霍夫曼重排反應則是以一級醯胺和NBS與強鹼（如DBU）反應產生胺基甲酸酯。”哪个来源这么说的？原文标题"METHYL CARBAMATE FORMATION VIA MODIFIED HOFMANN REARRANGEMENT REACTIONS"，英文MODIFIED是什么意思？--Antigng（留言） 2015年7月7日 (二) 08:35 (UTC)
**：内容欠准确，请主编回应并改善上述问题。--食人魔国王Talk 2015年7月9日 (四) 02:35 (UTC)
thread_title:  挂disputed维护模板