The base-catalysed cyclisation of phenyl N-(2-hydroxybenzyl)-N-methylcarbamates is concerted
Literature Information
Publication Date
2002-12-11
DOI
10.1039/B209323P
Impact Factor
3.876
Authors
Vojeslav Štěrba, Oldřich Hrabík, Jaromír Kaválek, Jaromír Mindl, Andrew Williams
View Original
Abstract
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.
Related Literature
Carbon-supported iron–ionic liquid: an efficient and recyclable catalyst for benzylation of 1,3-dicarbonyl compounds with alcohols
P. Moriel, A. B. García
2014-07-08
Paper
DOI: 10.1039/C4GC00755G
Solvent-free mechanochemical synthesis of alane, AlH3: effect of pressure on the reaction pathway
S. Gupta, T. Kobayashi
2014-07-22
Paper
DOI: 10.1039/C4GC00998C
Expanding the scope of enzymatic carboligation reactions in flow-mode: production of optically active tertiary alcohols with packed-bed micro-bioreactors
P. P. Giovannini, O. Bortolini, A. Cavazzini, R. Greco, G. Fantin, A. Massi
2014-06-09
Paper
DOI: 10.1039/C4GC00838C
Preparation of a macroscopic, robust carbon-fiber monolith from filamentous fungi and its application in Li–S batteries
Liyuan Zhang, Yangyang Wang, Wanting Yu, Baiwan Deng, Kai Zhang, Jiexi Wang
2014-06-13
Paper
DOI: 10.1039/C4GC00761A
Influence of precursor type on non-toxic hybrid inks for high-efficiency Cu2ZnSnS4 thin-film solar cells
Kyujin Kim, Inhyuk Kim, Yunjung Oh, Daehee Lee, Kyoohee Woo, Sunho Jeong, Jooho Moon
2014-07-10
Paper
DOI: 10.1039/C4GC00896K
Selective isomerization–carbonylation of a terpene trisubstituted double bond
Hanna Busch, Florian Stempfle, Sandra Heß, Etienne Grau, Stefan Mecking
2014-09-03
Communication
DOI: 10.1039/C4GC01233J
Gold supported on titania for specific monohydrogenation of dinitroaromatics in the liquid phase
Shuang-Shuang Liu, Xiang Liu, Lei Yu, Yong-Mei Liu, He-Yong He, Yong Cao
2014-06-26
Paper
DOI: 10.1039/C4GC00869C
Furfural from corn stover hemicelluloses. A mineral acid-free approach
Hilda Gómez Bernal, Luca Bernazzani
2014-05-15
Communication
DOI: 10.1039/C4GC00450G
Continuous production of sugars from pyrolysis of acid-infused lignocellulosic biomass
2014-06-17
Paper
DOI: 10.1039/C4GC00602J
Synthesis of 2-substituted pyrimidines and benzoxazoles via a visible-light-driven organocatalytic aerobic oxidation: enhancement of the reaction rate and selectivity by a base
Lin Wang, Zhi-Gang Ma, Xiao-Jing Wei, Qing-Yuan Meng, Deng-Tao Yang, Shao-Fu Du, Zi-Fei Chen, Li-Zhu Wu, Qiang Liu
2014-06-18
Communication
DOI: 10.1039/C4GC00337C
You might also like
Compound Q&A
How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?
2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...
615-45-22-Methylbenzene-1,4-...
Compound Q&A
Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?
(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...
132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A
What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?
(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...
871826-15-2(6-Chloropyridazin-3...
Compound Q&A
What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?
2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...
77772-72-62-Fluoro-3-methylphe...
Compound Q&A
What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?
When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...
177476-75-43-Methoxy-4-nitroben...
Compound Q&A
What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?
When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...
211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A
What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?
4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...
90347-86-74-Ethynylbenzamide
Compound Q&A
What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?
3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...
186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A
What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?
(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...
500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A
What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?
Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...
102196-18-92-[4-(Hydroxymethyl)...
Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
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.
Recommended Compounds
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.