Reaction of the ambident electrophile dimethyl carbonate with the ambident nucleophile phenylhydrazine

Rosamilia AE; Aric F; Tundo P

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Reaction of the ambident electrophile dimethyl carbonate with the ambident nucleophile phenylhydrazine

机译：环境亲电碳酸二甲酯与环境亲核苯肼的反应

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To explore the ambident electrophilic reactivity of dimethyl carbonate (DMC), reactions with the ambident nucleophile phenylhydrazine were investigated. When a Bronsted base was used, selective carboxymethylation occurred at N-1, after that several other compounds were produced selectively utilizing various conditions. Formation of these compounds was explained by using the Hard-Soft Acid-Base (HSAB) theory. Catalysis by some metal salts altered the reactivity of phenylhydrazine, which effected selective carboxymethylation at N-2 of phenylhydrazine instead.

机译：为了探索碳酸二甲酯（DMC）的亲电反应性，研究了与亲核亲核剂苯肼的反应。当使用布朗斯台德碱时，在N-1处发生选择性羧甲基化，此后利用各种条件选择性地产生了几种其他化合物。这些化合物的形成通过使用硬软酸碱（HSAB）理论进行了解释。某些金属盐的催化作用改变了苯肼的反应性，从而影响了苯肼在N-2处的选择性羧甲基化。

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《The Journal of Organic Chemistry》 |2008年第4期|共4页
作者
Rosamilia AE; Aric F; Tundo P;
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正文语种 eng
中图分类有机化学;
关键词
SOFT ACIDS; METHYLATION; HYDRAZINES; ACIDITIES; CHEMISTRY; BASES; HARD;

机译：软酸;甲基化;肼;酸;化学;碱;硬;

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1. Reaction of the ambident electrophile dimethyl carbonate with the ambident nucleophile phenylhydrazine [J] . Rosamilia AE, Aric F, Tundo P The Journal of Organic Chemistry . 2008,第4期

机译：环境亲电碳酸二甲酯与环境亲核苯肼的反应
2. Regiochemistry of an ambident cyclic ketene-N,O-acetal nucleophile and its anion toward electrophiles [J] . Yingquan Song, Hondamuni I. De Silva, William P. Henry Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2011,第35期

机译：环烯酮-N，O-缩醛亲核体及其阴离子对亲电体的区域化学
3. Steroidal δ-Alkenyl Oximes as Ambident Nucleophiles: Electrophile- Induced Formation of Oxazepane Derivatives in the Bis-Estrone Series [J] . Erzsébet Mernyáka Zsolt Bikádib Eszter Hazaib László Márkc Gyula Schneidera and János Wölfling*a Letters in Organic Chemistry . 2008,第1期

机译：类固醇亲核的类固醇δ-烯基肟：在Bis-Estrone系列中由亲电试剂诱导的氧杂庚烷衍生物的形成
4. DIMETHYL CARBONATE: GREEN SOLVENT AND AMBIDENT REAGENT [C] . PIETRO TUNDO, F. ARICO, ANTHONY E. ROSAMILIA, NATO advanced study institute on new organic chemistry reactions and methodologies for green production; 20061029-1110; Lecce(IT) . 2006

机译：碳酸二甲酯：绿色溶剂和邻位试剂
5. Utilizing allylic alcohols as both electrophiles and nucleophiles in gold-catalyzed reactions. [D] . Ketcham, John Michael. 2013

机译：在金催化的反应中同时使用烯丙醇作为亲电子试剂和亲核试剂。
6. Reactions of glycidyl derivatives with ambident nucleophiles; part 2: amino acid derivatives [O] . Gerald Dyker, Andreas Thöne, Gerald Henkel 2007

机译：缩水甘油基衍生物与环境亲核试剂的反应；第2部分：氨基酸衍生物
7. Reaction of the Ambident Electrophile Dimethyl Carbonate with the Ambident Nucleophile Phenylhydrazine [O] . ROSAMILIA A, ARICO' F, TUNDO P. 2008

机译：环境亲电性碳酸二甲酯与环境亲核试剂苯肼的反应
8. Reaction of gem-Dichloroallyllithium with Aldehydes, Ketones, and Other Organic Substrates. An Example of Electronic Control of Regioselectivity in the Reactions of an Ambident Nucleophile. [R] . Seyferth, D., Murphy, G. J., Mauze, B. 1977

机译：宝石 - 二氯烯丙基锂与醛，酮和其他有机基质的反应。环境亲核试剂反应中区域选择性的电子控制实例。

Reaction of the ambident electrophile dimethyl carbonate with the ambident nucleophile phenylhydrazine

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