The base-catalysed cyclisation of phenyl N-(2-hydroxybenzyl)-N-methylcarbamates is concerted

文献信息

发布日期 2002-12-11
DOI 10.1039/B209323P
影响因子 3.876
作者

Vojeslav Štěrba, Oldřich Hrabík, Jaromír Kaválek, Jaromír Mindl, Andrew Williams


查看原文

摘要

The kinetics of the cyclisation in aqueous solution of phenyl-(2-hydroxybenzyl)-N-methylcarbamates to 3-methyl-3,4-dihydrobenzo[e][1,3]oxazin-2-ones and phenolate ions fit the rate law:kobs = kc/(1 + [H3O+]/Ka)The values of kc and pKa fit Brønsted equations against the pKa's of the corresponding free phenols but the system does not conform to the reactivity–selectivity hypothesis. The values of the Brønsted parameters βY and βX vary as a function of Y and X according to the equations:βX = −0.179pKaHY + 0.87βY = −0.179pKaHX + 2.30The magnitude and sign of the Cordes–Thornton cross-interaction coefficient pXY (−0.179) rule out a stepwise mechanism involving a tetrahedral intermediate and is consistent with a concerted displacement mechanism. A similar concerted mechanism is proposed for the base-catalysed cyclisation of phenyl-N-(2-hydroxyphenyl)-N-methylcarbamate esters to benzoxazol-2-ones.

相关文献

Hydrothermal saline promoted grafting: a route to sulfonic acid SBA-15 silica with ultra-high acid site loading for biodiesel synthesis

C. Pirez, A. F. Lee, J. C. Manayil, C. M. A. Parlett, K. Wilson

2014-07-24 Communication

DOI: 10.1039/C4GC01139B

Transitioning organic synthesis from organic solvents to water. What's your E Factor?

Bruce H. Lipshutz, Subir Ghorai

2014-07-02 Critical Review

DOI: 10.1039/C4GC00503A

Visible-light-induced photocatalytic formyloxylation reactions of 3-bromooxindoles with water and DMF: the scope and mechanism

You-Quan Zou, Wei Guo, Feng-Lei Liu, Liang-Qiu Lu, Jia-Rong Chen

2014-05-08 Paper

DOI: 10.1039/C4GC00647J

Enzymatic synthesis of ionic responsive lignin nanofibres through surface poly(N-isopropylacrylamide) immobilization

Guangzheng Gao, Muzaffer A. Karaaslan, John F. Kadla, Frank Ko

2014-06-23 Paper

DOI: 10.1039/C4GC00757C

Hydrogenation of levulinic acid to γ-valerolactone by Ni and MoOx co-loaded carbon catalysts

Shota Kanno, Kenichi Kon

2014-06-05 Paper

DOI: 10.1039/C4GC00735B

New bi-functional zinc catalysts based on robust and easy-to-handle N-chelating ligands for the synthesis of cyclic carbonates from epoxides and CO2 under mild conditions

Rongchang Luo, Xiantai Zhou, Wuying Zhang, Zhongxiu Liang, Jun Jiang, Hongbing Ji

2014-06-26 Paper

DOI: 10.1039/C4GC00671B

Regioselective acetylation of carbohydrates and diols catalyzed by tetramethyl-ammonium hydroxide in water

Yuchao Lu, Peng Wei, Yuxin Pei, Hengfu Xu, Xiaoting Xin

2014-07-31 Communication

DOI: 10.1039/C4GC00770K

Furfural from corn stover hemicelluloses. A mineral acid-free approach

Hilda Gómez Bernal, Luca Bernazzani

2014-05-15 Communication

DOI: 10.1039/C4GC00450G

Electrodeposited CZTS solar cells from Reline electrolyte

Hao Chen, Qinyan Ye, Xulin He, Jingjing Ding, Yongzheng Zhang, Junfeng Han, Jiang Liu, Cheng Liao, Jun Mei, Woonming Lau

2014-05-13 Paper

DOI: 10.1039/C4GC00142G

您可能还喜欢

化合物问答

N-2,2-丙烯基-2-丙烯酰胺(CAS号:2555-13-7)通常如何合成?

N-2,2-丙烯基-2-丙烯酰胺通常通过丙烯酰胺与丙烯基卤化物的缩合反应合成。该反应通常在温和的条件下进行,使用适量的碱如吡啶作为催化剂。反应的选择性良好,产率...

2555-13-7N-Allylacrylamide
化合物问答

什么是1,2-二碘四氟代乙烷(CAS号:354-65-4)?

1,2-二碘四氟代乙烷是一种有机化合物,化学式为C2F4I2,CAS号为354-65-4。它是一种无色透明液体,具有特殊的化学性质和物理性质,包括高沸点、低挥发...

354-65-41,1,2,2-Tetrafluoro-...
化合物问答

3-溴-1H-吡咯[3,2-c]吡啶-4-碳腈(CAS号:1000341-71-8)适用哪些法规指南?

根据GHS(全球化学品统一分类和标签制度),3-溴-1H-吡咯[3,2-c]吡啶-4-碳腈被归类为第2类易燃液体。在欧盟,该化合物需要符合REACH法规的要求,...

1000341-71-83-Bromo-1H-pyrrolo[3...
化合物问答

1-氯甲基萘磺酸(CAS号:87491-79-0)安全吗?

1-氯甲基萘磺酸在使用时需要谨慎,因为它具有一定的刺激性和腐蚀性。操作时应佩戴适当的防护装备,如防化服、手套、护目镜等,避免直接接触皮肤和吸入其蒸汽。

87491-79-01-((Chloromethyl)sul...
化合物问答

二氯(二环戊二烯)铂(CAS号:12083-92-0)的主要用途是什么?

该化合物主要用于催化剂领域,特别是在有机合成中的催化氧化反应以及作为某些药物合成的中间体。此外,它还被研究用于纳米材料的制备。

12083-92-0(1S,7R)-Tricyclo[5.2...
化合物问答

3-溴-7-氯噻吩并[3,2-b]吡啶-6-甲腈(CAS号:798574-82-0)安全吗?

3-溴-7-氯噻吩并[3,2-b]吡啶-6-甲腈在处理时需要谨慎,因其含有溴和氯等强卤素,可能具有一定的刺激性和腐蚀性。使用时应佩戴适当的个人防护装备,避免皮肤...

798574-82-03-Bromo-7-chlorothie...
化合物问答

(R)-1-((R)-2-(2’-二环己基膦苯基)三戊铁基]乙基(双-3,5-三氟甲基苯基)膦(CAS号:494227-32-6)的主要用途是什么?

该化合物主要用于有机合成领域,特别是作为催化剂或配体,在有机合成反应中发挥重要作用。此外,它还可能应用于催化加氢反应、偶联反应等。

494227-32-6Walphos SL-W008-1
化合物问答

3-[6-(Diphenylphosphoryl)-2-naphthyl]-1,10-phenanthroline(CAS号:1480371-38-7)安全吗?

3-[6-(Diphenylphosphoryl)-2-naphthyl]-1,10-phenanthroline在正常使用条件下相对安全,但在操作时应穿戴适当...

1480371-38-73-[6-(Diphenylphosph...
化合物问答

在合成中是否有ETHYL 2-(4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)CYCLOHEX-3-ENYL)ACETATE(CAS号:1166829-70-4)的替代品?

可以考虑使用类似结构的化合物作为替代品,如2-(4-环戊基环己烯基)乙酸酯,这种化合物在结构上相似,可能在某些合成路径中作为替代品。

1166829-70-4Ethyl [4-(4,4,5,5-te...
化合物问答

如何处理含有3-(3-氨基丙基)丙酮缩甘油(CAS号:131606-42-3)的废料?

处理含有3-(3-氨基丙基)丙酮缩甘油的废料时,首先应确保遵守当地的环保法规。对于危险废物,应进行分类收集,然后送至专业的废物处理设施进行焚烧或安全填埋。在处理...

131606-42-33-[(2,2-Dimethyl-1,3...

来源期刊

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
自引率: 10.3%
年发文量: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

推荐供应商

免责声明
本页面提供的学术期刊信息仅供参考和研究使用。我们与任何期刊出版商均无关联,也不处理投稿事宜。如有投稿相关咨询,请直接联系相关期刊出版商。
如发现页面信息有误,请发送邮件至 support@chemtradehub.com 联系我们。我们将及时核实并处理您的问题。