The Reversible Consecutive Mechanism for the Reaction of Trinitroanisole with Methoxide Ion

2011 ◽  
Vol 76 (5) ◽  
pp. 1250-1256 ◽  
Author(s):  
Vernon D. Parker ◽  
Zhao Li ◽  
Kishan L. Handoo ◽  
Weifang Hao ◽  
Jin-Pei Cheng
Keyword(s):  

1970 ◽  
Vol 23 (5) ◽  
pp. 957 ◽  
Author(s):  
MEC Biffin ◽  
J Miller ◽  
AG Moritz ◽  
DB Paul

Contrasting behaviour is observed when 2- and 4-methoxy-3,5-dinitropyridine interact with methoxide ion in dimethyl sulphoxide. The 4-methoxy compound affords both methine and acetal sigma complexes, the latter being thermodynamically more stable. The interconversion is catalysed by methanol. Labelling experiments have established that the sigma complex from the 2-methoxypyridine is formed by addition at C6; no conversion into the acetal could be effected. These observations are rationalized in terms of differential steric and solvation effects. Demethylation and rearrangement reactions of 4-methoxy-3,5-dinitropyridine are reported.



1986 ◽  
Vol 51 (11) ◽  
pp. 2125-2126 ◽  
Author(s):  
Audrey Di Lorenzo ◽  
Paolo Mencarelli ◽  
Franco Stegel
Keyword(s):  


1974 ◽  
Vol 96 (3) ◽  
pp. 656-659 ◽  
Author(s):  
David R. Yarkony ◽  
Henry F. Schaefer ◽  
Stephen Rothenberg


1984 ◽  
Vol 62 (9) ◽  
pp. 1840-1844 ◽  
Author(s):  
Karl R. Kopecky ◽  
Alan J. Miller

Treatment of methyl hydrogen decahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a,8a-dicarboxylate with lead tetraacetate in benzene – acetic acid replaces the carboxyl group by an acetoxy group. Hydrolysis of this product with 25% sulfuric acid at 130 °C forms 8a-hydroxydecahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a-carboxylic acid 10. The reaction between 10 and benzenesulfonyl chloride in pyridine containing triethylamine at 95 °C produces anti-sesquinorbornene 1 in 34% yield. In the absence of triethylamine 1 is converted to the hydrochloride. The iodohydroperoxide of 1 is converted by silver acetate at 0 °C to the diketone in a luminescent reaction. The 1,2-dioxetane could not be isolated. Decahydro-1,4:5,8-exo,exo-dimethanonaphthalene-4a,8a-dicarboxylic anhydride is converted slowly by methoxide ion in methanol at 150 °C to the monomethyl ester which then undergoes demethylation. The isomeric exo,endo anhydride undergoes reaction readily with methoxide ion at 80 °C.



2006 ◽  
Vol 19 (1) ◽  
pp. 61-67 ◽  
Author(s):  
Jiří Hanusek ◽  
Miloš Sedlák ◽  
Petr Jansa ◽  
Vojeslav Štěrba
Keyword(s):  


1975 ◽  
Vol 97 (20) ◽  
pp. 5889-5896 ◽  
Author(s):  
John A. Zoltewicz ◽  
Terence M. Oestreich ◽  
Alan A. Sale


1972 ◽  
Vol 94 (16) ◽  
pp. 5781-5786 ◽  
Author(s):  
I. R. Bellobono ◽  
A. Gamba ◽  
G. Sala ◽  
M. Tampieri


1991 ◽  
Vol 56 (22) ◽  
pp. 6331-6336 ◽  
Author(s):  
Giancarlo Doddi ◽  
Gianfranco Ercolani ◽  
Paolo Mencarelli ◽  
Carlo Scalamandre
Keyword(s):  


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