Cycloadditions of 1H-1,3-Benzazaphospholes with o-Chloranil

Joachim W. Heinicke; Nidhi Gupta; Peter Mayer; Konstantin Karaghiosoff

首页> 外文期刊>Zeitschrift fur Anorganische und Allgemeine Chemie >Cycloadditions of 1H-1,3-Benzazaphospholes with o-Chloranil

【24h】

Cycloadditions of 1H-1,3-Benzazaphospholes with o-Chloranil

机译：1H-1,3-苯并磷硅氧烷与O-Chloranil的环加成

获取原文

获取原文并翻译 | 示例

掌桥外文数据库（机构版） >>

开具论文收录证明 >>

文献代查 >>

页面导航

摘要
著录项
相似文献
相关主题

摘要

NH-Functional 1H-1,3-benzazaphospholes 1a-1c and ochloranil (tetrachloro-o-benzoquinone - TCBQ) undergo rapid [1+4]- cycloaddition in a 1:2 molar ratio to give 2a-2c as high-melting zwitterionic σ~6λ~5-phosphorus compounds. In the case of 2a the yield is high (rel. to TCBQ) even if the reactants were used in a 1:0.5 molar ratio. For the 2-tert-butyl-substituted compounds 2b and 2c the yields were significantly lower, in part by unidentified byproducts. Addition of excess TCBQ to crude 2c containing unconverted 1c did not increase but strongly decrease the amount of 2c. Crystallization and XRD analysis led to detection of a minor side or consecutive product 3c, formally corresponding to P=C bond cleavage and [1+4] cycloaddition of three equivalents TCBQ, two at the phosphinidene and one at the arylaminocarbene end. NMR spectroscopic data of 2a-2c including conclusive 13C data for 2a give evidence of the structures of the new compounds.

机译：NH功能性1H-1,3-苯扎膦酸盐1a-1c和赭氯苯胺（四氯邻苯醌-TCBQ）以1:2的摩尔比进行快速[1+4]环加成，得到2a-2c作为高熔点两性离子σ~6λ~5-磷化合物。在2a的情况下，即使反应物的摩尔比为1:0.5，产率也很高（相对于TCBQ）。对于2-叔丁基取代的化合物2b和2c，产率明显较低，部分原因是未知的副产物。向含有未转化1c的原油2c中添加过量TCBQ不会增加，但会显著降低2c的含量。结晶和XRD分析导致检测到次要侧或连续产物3c，正式对应于P=C键断裂和三种当量TCBQ的[1+4]环加成，两种在亚膦端，一种在芳基氨基碳烯端。2a-2c的NMR光谱数据，包括2a的确凿13C数据，为新化合物的结构提供了证据。

著录项

来源
《Zeitschrift fur Anorganische und Allgemeine Chemie》 |2020年第13期|共5页
作者
Joachim W. Heinicke; Nidhi Gupta; Peter Mayer; Konstantin Karaghiosoff;
展开▼
作者单位

Institut für Biochemie Universit?t Greifswald 17487 Greifswald Germany;

Institut für Biochemie Universit?t Greifswald 17487 Greifswald Germany;

Department Chemie Ludwig-Maximilians-Universit?t München 81377 München Germany;

Department Chemie Ludwig-Maximilians-Universit?t München 81377 München Germany;

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类化学;
关键词
Phosphorus heterocycles; P=C bond; Cycloaddition; Quinones; Zwitterionic P-tris(chelates);

机译：磷杂环;p = c键;环加成;Quinones;两倍离子P-TRIS（螯合物）;

相似文献

外文文献
中文文献
专利

1. Synthesis, Structure and Biological Activities of 2-(1H-1,2,3-Benzotriazol-1-yl)-1-(4-methylphenyl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone [J] . 高等学校化学研究（英文版） . 2006,第004期
2. Metalated 1,3-Azaphospholes: 1H-1,3-Benzazaphosphole and 1,3-Benzazaphospholide Tungsten(0) and Tungsten(II) Complexes [J] . Joachim Heinicke, Anushka Surana, Normen Peulecke, European journal of inorganic chemistry . 2001,第10期

机译：金属化的1,3-氮杂磷化物：1H-1,3-苯并氮杂磷和1,3-苯并氮杂磷钨（0）和钨（II）配合物
3. Synthesis of 1H-1,3-benzazaphospholes: substituent influence and mechanistical aspects [J] . Joachim Heinicke, Nidhi Gupta, Anushka Surana, Tetrahedron . 2001,第50期

机译：1H-1,3-苯并氮杂唑的合成：取代基的影响和机理
4. 1H-1,3-Benzazaphospholes: The Organometallic Route and a New Three-Step Synthesis with Reductive Ring Closure [J] . Raj K. Bansal, Neelima Gupta, Joachim Heinicke, Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 1999,第2期

机译：1H-1,3-Benzazaphospholes：有机金属路线和带有还原环封闭作用的新三步合成
5. (cest2017_00558) Photocatalytic Degradation of o-Chloranil on Nano Crystalline Cellulose Doped Titania [C] . Moodley V, Maddila S, Jonnalagadda S.B. International Conference on Environmental Science and Technology . 2017

机译：（CEST2017_00558）在纳米结晶纤维素上掺杂二氧化钛的O-Chloranil的光催化降解
6. Studies on aza-cycloaddition: Part 1. Intramolecular ketene-imine cycloaddition Part 2. Iminium ion-mediated [4+2] cycloaddition [D] . Park, Jung-hyun 2010

机译：氮杂-环加成反应的研究：第1部分。分子内烯酮-亚胺环加成反应；第2部分。亚胺离子介导的[4 + 2]环加成反应
7. 1-{[4′-(1H-1,2,4-Triazol-2-ium-1-ylmethyl)biphenyl-4-yl]methyl}-1H-1,2,4-triazol-2-ium bis(3-carboxy-5-iodobenzoate)–5-iodobenzene-3,5-dicarboxylic acid–water (1/2/2) [O] . Kou-Lin Zhang, Ye Deng, Seik Weng Ng 2015

机译：1-{[[4'-（1H-1,2,4-三唑-2-基-1-基甲基）联苯-4-基]甲基} -1H-1,2,4-三唑-2-基双（ 3-羧基-5-碘苯甲酸酯）–5-碘苯-3,5-二羧酸–水（1/2/2）
8. Azide–Alkyne Cycloaddition En Route to 1H-1,2,3-Triazole-Tethered Isatin–Ferrocene, Ferrocenylmethoxy–Isatin, and Isatin–Ferrocenylchalcone Conjugates: Synthesis and Antiproliferative Evaluation [O] . Amandeep Singh, Sourav Taru Saha, Shanen Perumal, 2018

机译：静止至1H-1,2,3-三唑丝丝素，铁烯基甲氧基 - Isatin和Isatin-FerrocenylChalcone缀合物的途径 - 烷基 - 炔烃环加装入途中：合成和抗增殖评估
9. Initial Submission: Teratology Study of 1H-1,24-Thiazole-1-Propanenitrile, Alpha-Butyl-Alpha- (4-Chlorophenyl)-inRats with Cover Letter dated 08/12/1992 [R] . 1992

机译：初次提交：1H-1,24-噻唑-1-丙腈，α-丁基-α-（4-氯苯基）-inRats的畸形学研究，封面信函日期为1992年12月8日

Cycloadditions of 1H-1,3-Benzazaphospholes with o-Chloranil

摘要

著录项

相似文献

相关主题

期刊订阅