Relative Reactivity of Maleic Anhydride and Sulfur Dioxide in 1,4-Addition Reactions to 2,3-Dimethyl-1,3-butadiene

1960 ◽  
Vol 82 (14) ◽  
pp. 3614-3619 ◽  
Author(s):  
Oliver Grummitt ◽  
Andrew L. Endrey
Keyword(s):  
Sulfur Dioxide ◽  
Maleic Anhydride ◽  
Relative Reactivity ◽  
Addition Reactions

Ionic dimerisation of trifluoropropenenitrile and its addition reactions with methyl trifluoropropenoate

1980 ◽  
Vol 45 (2) ◽  
pp. 406-414 ◽  
Author(s):  
Jiří Svoboda ◽  
Oldřich Paleta ◽  
Václav Dědek
Keyword(s):  
Reaction Mechanism ◽  
Proton Transfer ◽  
Substituent Effect ◽  
Solvent Molecule ◽  
Addition Product ◽  
Potassium Fluoride ◽  
Relative Reactivity ◽  
Addition Reactions ◽  
Tertiary Amines ◽  
Optimum Conditions

Dimerisation of trifluoropropenenitrile (I) in the presence of potassium fluoride and tertiary amines afforded a mixture of stereoisomeric perfluoro-4-methyl-pentenedinitriles (II), higher-boiling compounds, and 2,3,3,3-tetrafluoropropanenitrile (III) which arises by proton transfer from the solvent molecule. Under optimum conditions, product II was obtained in about 50% yield. Reaction of the nitrile I with methyl trifluoropropenoate (IV) gave, besides the dimers II and V, the product of addition of the nitrile I to the propenoate, IV, i.e. methyl 4-cyanoperfluoro-2-pentenoate (VI), and the addition product of the propenoate IV to the nitrile I, i.e. methyl 4-cyanoperfluoro-2-methyl-3-butenoate (VII). The relative reactivity if I and IV is discussed. The ratio of stereoisomers in II, V, VI and VII indicates that the magnitude of the steric substituent effect, operating in the reaction mechanism, decreases in the order -CFCF3.(COOCH3) > -CFCF3(CN) > -COOCH3 > -CN.

Relative Reactivities of 1,1,1-Trichloroethane and 1,1,1-Trichlorotrifluoroethane in Competitive Addition Reactions

1992 ◽  
Vol 57 (6) ◽  
pp. 1291-1298 ◽  
Author(s):  
František Adámek ◽  
Milan Hájek ◽  
Zbyněk Janoušek
Keyword(s):  
Free Radical ◽  
Reaction Mechanism ◽  
Relative Reactivity ◽  
Addition Reactions ◽  
Radical Initiation ◽  
Amine Complexes ◽  
Free Radical Initiation ◽  
Ru Complexes ◽  
Radical Initiators

Relative reactivity of CH3CCl3 and CF3CCl3 measured in competitive addition reactions with 1-hexene in the presence of free radical initiators or Cu, Pd and Ru complexes was found to depend on the type of catalyst. The unusual course of the reaction has been found in the additions catalyzed with copper(I)-amine complexes where CH3CCl3 in competition with CF3CCl3 was completely unreactive. The results have been explained in terms of the change of reaction mechanism and compared with classical free radical initiation.

Relative reactivity of vinylsilanes in nucleophilic addition reactions

1968 ◽  
Vol 17 (9) ◽  
pp. 1969-1971
Author(s):  
N. S. Nametkin ◽  
V. N. Perchenko ◽  
I. A. Grushevenko ◽  
G. L. Kamneva
Keyword(s):  
Nucleophilic Addition ◽  
Relative Reactivity ◽  
Addition Reactions

Addition Reactions of Maleic Anhydride to a Disilene and a Tetrasilabuta-1,3-diene:  Formation of Bi- and Tetracyclic Compounds1,2

2001 ◽  
Vol 20 (12) ◽  
pp. 2451-2453 ◽  
Author(s):  
Sven Boomgaarden ◽  
Wolfgang Saak ◽  
Manfred Weidenbruch ◽  
Heinrich Marsmann
Keyword(s):  
Maleic Anhydride ◽  
Addition Reactions

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.

Sign in / Sign up

Export Citation Format

Share Document