ChemInform Abstract: Synthesis of (3S,4R)-3,4-Isopropylidenedioxy-1-pyrroline-N-oxide, an Enantiopure Functionalized Cyclic Nitrone; Cycloaddition Reactions with Dimethyl Maleate and Dimethyl Fumarate.

ChemInform ◽  
2010 ◽  
Vol 29 (50) ◽  
pp. no-no
Author(s):  
M. CLOSA ◽  
R. H. WIGHTMAN
Keyword(s):  
Dimethyl Fumarate ◽  
Cycloaddition Reactions ◽  
Dimethyl Maleate

Cycloaddition reactions of the anhydro-4-hydroxythiazolium hydroxide system with dimethyl maleate and dimethyl fumarate

Tetrahedron ◽  
1978 ◽  
Vol 34 (24) ◽  
pp. 3525-3530 ◽  
Author(s):  
A. Robert ◽  
M. Baudy ◽  
A. Foucaud ◽  
L. Golic ◽  
B. Stanovnik
Keyword(s):  
Dimethyl Fumarate ◽  
Cycloaddition Reactions ◽  
Dimethyl Maleate

E,E- and E,Z-α-phenyl-α′-acetoxyorthoquinodimethane: steric and electronic control of cycloaddition reactions

1986 ◽  
Vol 64 (4) ◽  
pp. 793-798 ◽  
Author(s):  
James L. Charlton ◽  
Mian M. Alauddin ◽  
Glenn H. Penner
Keyword(s):  
Maleic Anhydride ◽  
Electronic Properties ◽  
Dimethyl Fumarate ◽  
Diels Alder ◽  
Addition Reactions ◽  
Cycloaddition Reactions ◽  
Electronic Control ◽  
Dimethyl Maleate ◽  
Cis And Trans ◽  
Abinitio Calculations

E,E- and E,Z-α-phenyl-α′-acetoxyorthoquinodimethanes have been prepared from the corresponding cis- and trans-1-acetoxy-3-phenyl-1,3-dihydrobenzo[c]thiophene-2,2-dioxides. The regio- and diastereoselectivity of the addition reactions with dimethyl fumarate, dimethyl maleate, maleic anhydride, and methyl crotonate have been determined. Abinitio calculations have been carried out on orthoquinodimethane and its α-phenyl and α-oxy derivatives. A correlation has been made between the steric and electronic properties of the orthoquinodimethanes and the regio- and diastereoselectivity of their Diels–Alder reactions.

Preparation of 1-thio and 1-amino substituted 1,3-dihydrobenzo[c]thiophene 2,2-dioxides

1987 ◽  
Vol 65 (3) ◽  
pp. 482-486 ◽  
Author(s):  
Zafar Khan ◽  
Tony Durst
Keyword(s):  
Phenyl Group ◽  
Dimethyl Fumarate ◽  
Cycloaddition Reactions ◽  
Amino Groups

The 1-hydroxy substituent in 1-hydroxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxides is readily replaced by alkoxy, alkylthio, and amino groups. These compounds serve as precursors of alkoxy, alkylthio, and amino substituted o-quinodimethanes. Cycloaddition reactions between a series of 1,4-disubstituted o-quinodimethanes bearing a phenyl group and one of the above heteroatoms, and typical dienophiles such as dimethyl fumarate and methyl crotonate were carried out. The phenyl group controlled both the regiochemistry and stereochemistry of these cycloaddition reactions, with the major products being trans-1-phenyl-2-carbomethoxytetrahydronaphthalenes. The amino substituted o-quinodimethanes were trapped only by dimethyl fumarate.

Reactions of a New Family of Amide Derivatives of Phenanthridinium Azomethine Ylides with Dipolarophiles

1999 ◽  
Vol 64 (12) ◽  
pp. 1993-2006 ◽  
Author(s):  
Martin Trávníček ◽  
Jiří Pospíšil ◽  
Milan Potáček
Keyword(s):  
Nmr Spectroscopy ◽  
Cycloaddition Reaction ◽  
Dimethyl Fumarate ◽  
Azomethine Ylides ◽  
New Family ◽  
Amide Derivatives ◽  
Dimethyl Maleate ◽  
Derivatives Of

Reaction of a series of N-alkyl- and N,N-dialkylbromoacetamides 1a-1e with phenanthridine afforded quaternary phenanthridinium salts 2a-2e. These compounds treated with triethylamine form azomethine ylides which undergo a cycloaddition reaction with activated C=C bond, giving 3-(N-alkylcarbamoyl)-1,2,3,12b-tetrahydropyrrolo[1,2-f]phenanthridines 3a-3e, 4c, 5c, 6c or 3-(N-alkylcarbamoyl)-2,3-dihydropyrrolo[1,2-f]phenanthridine 7c. Their stereochemistry was studied by NMR spectroscopy. The best results were obtained with fumaronitrile as a dipolarophile. It has been found that the ylides react in syn conformations but if 1-adamantyl moiety is bound to the ylide, it reacts in anti conformation, too. The azomethine ylides show a very poor reactivity towards dimethyl fumarate or dimethyl maleate. Yet we could prepare products for ylide bearing 1-adamantyl group.

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