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F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
( R e d i r e c t e d f r o m M e t h o x y l )
On a benzene ring , the Hammett equation classifies a methoxy substituent at the para position as an electron-donating group , but as an electron-withdrawing group if at the meta position. At the ortho position, steric effects are likely to cause a significant alteration in the Hammett equation prediction which otherwise follows the same trend as that of the para position.
Occurrence
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The simplest of methoxy compounds are methanol and dimethyl ether . Other methoxy ethers include anisole and vanillin . Many metal alkoxides contain methoxy groups, such as tetramethyl orthosilicate and titanium methoxide . Esters with a methoxy group can be referred to as methyl esters, and the —COOCH3 substituent is called a methoxycarbonyl.[1]
Biosynthesis
[ edit ]
In nature, methoxy groups are found on nucleosides that have been subjected to 2 ′-O -methylation , for example in variations of the 5 ′-cap structure known as cap-1 and cap-2. They are also common substituents in O -methylated flavonoids , whose formation is catalyzed by O-methyltransferases that act on phenols , such as catechol-O -methyl transferase (COMT). Many natural products in plants, such as lignins , are generated via catalysis by caffeoyl-CoA O -methyltransferase .[2]
Methoxylation
[ edit ]
Organic methoxides are often produced by methylation of alkoxides.[3] [4] Some aryl methoxides can be synthesized by metal-catalyzed methylation of phenols , or by methoxylation of aryl halides .[5] [6]
References
[ edit ]
^ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Lignin Biosynthesis". Annu. Rev. Plant Biol . 54 (1 ): 519–46. doi :10.1146/annurev.arplant.54.031902.134938 . PMID 14503002 .
^ Scarrow, J. A.; Allen, C. F. H. (1933). "Methoxyacetonitrile". Org. Synth . 13 : 56. doi :10.15227/orgsyn.013.0056 .
^ Cornella, Josep; Zarate, Cayetana; Martin, Ruben (2014). "Ni-catalyzed Reductive Cleavage of Methyl 3-Methoxy-2-Naphthoate" . Org. Synth . 91 : 260–272. doi :10.15227/orgsyn.091.0260 .
^ Cheung, Chi Wai; Buchwald, Stephen L. (2 August 2013). "Mild and General Palladium-Catalyzed Synthesis of Methyl Aryl Ethers Enabled by the Use of a Palladacycle Precatalyst" . Organic Letters . 15 (15 ): 3998–4001. doi :10.1021/ol401796v . PMC 3776604 . PMID 23883393 .
^ Tolnai, Gergely L.; Pethő, Bálint; Králl, Péter; Novák, Zoltán (13 January 2014). "Palladium-Catalyzed Methoxylation of Aromatic Chlorides with Borate Salts". Advanced Synthesis & Catalysis . 356 (1 ): 125–129. doi :10.1002/adsc.201300687 .
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Methoxy_group&oldid=1230264252 "
C a t e g o r i e s :
● O - m e t h y l a t i o n
● A l k o x y g r o u p s
● M e t h o x y c o m p o u n d s
H i d d e n c a t e g o r i e s :
● A r t i c l e s w i t h s h o r t d e s c r i p t i o n
● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 2 1 J u n e 2 0 2 4 , a t 1 8 : 0 3 ( U T C ) .
● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n .
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