High-Pressure Influence on the Rate of Diels-Alder Cycloaddition Reactions of Maleic Anhydride with Some Dienes

2013 ◽  
Vol 45 (9) ◽  
pp. 613-622 ◽  
Author(s):  
Vladimir D. Kiselev
Keyword(s):  
High Pressure ◽  
Maleic Anhydride ◽  
Diels Alder ◽  
Cycloaddition Reactions

scholarly journals Kinetic Analysis of the High-pressure Diels-Alder Reactions of Tropone with Maleic Anhydride and Norbornene

1985 ◽  
Vol 58 (9) ◽  
pp. 2490-2493 ◽  
Author(s):  
Hitoshi Takeshita ◽  
Shigeru Sugiyama ◽  
Toshihide Hatsui
Keyword(s):  
High Pressure ◽  
Maleic Anhydride ◽  
Kinetic Analysis ◽  
Diels Alder

High pressure organic chemistry. Part 17. Diels–Alder reaction of methyl palustrate with maleic anhydride and N-phenylmaleimide

1993 ◽  
pp. 2773-2776 ◽  
Author(s):  
Hiyoshizo Kotsuki ◽  
Masanori Kataoka ◽  
Kohtaro Matsuo ◽  
Shigeru Suetomo ◽  
Motoo Shiroc ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
High Pressure ◽  
Maleic Anhydride ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Effect of high pressure on the rate constant of the Diels-Alder reaction between furan and maleic anhydride

1990 ◽  
Vol 39 (3) ◽  
pp. 456-459 ◽  
Author(s):  
V. M. Zhulin ◽  
M. V. Kel'tseva ◽  
V. S. Bogdanov ◽  
Yu. D. Koreshkov ◽  
E. B. Kabotyanskaya
Keyword(s):  
High Pressure ◽  
Maleic Anhydride ◽  
Rate Constant ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Synthesis of functionalized hexahydro-, octahydro-, and decahydro-1H-phenalenes via Diels–Alder reactions of 1-methylene-4a-methoxycarbonyl-1,2,3,4,4a,5,6,7-octahydronaphthalene and related dienes

1993 ◽  
Vol 71 (9) ◽  
pp. 1463-1483 ◽  
Author(s):  
Edward Piers ◽  
Richard W. Friesen ◽  
Paul Kao ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Maleic Anhydride ◽  
Transition State ◽  
Methyl Acrylate ◽  
Diels Alder ◽  
Cycloaddition Reactions ◽  
Methoxycarbonyl Group ◽  
The Face ◽  
Group Reaction ◽  
Bicyclic Dienes

The results of a study of Diels–Alder reactions of the bicyclic dienes 6–8 with a variety of dienophiles are reported. Although 6 and 7 undergo cycloaddition reactions smoothly and efficiently, thermal Diels–Alder reactions of 8 are generally sluggish or, under the conditions investigated, do not proceed at all. Additions of tetracyanoethylene (TCNE) to 6–8 are highly face-selective, with preferential attack of the dienophile on the side of the dienes opposite to the angular methoxycarbonyl group. Reaction of 7 with maleic anhydride (MAN) is completely face-selective and proceeds preferentially via an endo transition state. Diels–Alder reactions of 6 and 7 with methyl acrylate (MAC) and nitroethylene (NE) are entirely regioselective, but the face-selectivities, which vary from ~2:1 to ~3:1, are rather low. The use of this chemistry as a method for the synthesis of functionalized, stereochemically defined, perhydro-1H-phenalenes is demonstrated.

Studying the effect of high pressure on the cycloaddition reactions of maleic anhydride and substituted anthracenes

2012 ◽  
Vol 87 (1) ◽  
pp. 160-162 ◽  
Author(s):  
V. D. Kiselev ◽  
I. I. Shakirova ◽  
D. A. Kornilov ◽  
E. A. Kashaeva ◽  
L. N. Potapova ◽  
...  
Keyword(s):  
High Pressure ◽  
Maleic Anhydride ◽  
Cycloaddition Reactions

Diels - Alder Reactions of 1,1-Bis(methylthio)ethene with Pyran-2-ones.

1998 ◽  
Vol 51 (5) ◽  
pp. 383 ◽  
Author(s):  
Robert W. Bates ◽  
Andrew J. Pratt ◽  
Phillip M. Rendle ◽  
Ward T. Robinson
Keyword(s):  
High Pressure ◽  
High Temperature ◽  
Diels Alder ◽  
Cycloaddition Reactions ◽  
Single Product

Bis(methylthio)ethene has been shown to undergo Diels–Alder cycloaddition reactions with a range of simple and aryl-fused pyran-2-ones. These reactions can be brought about under either high-temperature or high-pressure conditions. These reactions are all regiospecific and in each case only a single product is isolated, either the initial bridged adduct or an aromatized product generated through decarboxylation. Although this dienophile is less reactive than the corresponding oxygen analogue it is still possible for cycloaddition chemistry to compete effectively with decarboxylation chemistry.

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.

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