Dihydrothiophenes.10. The preparation and Diels–Alder reactions of some sulfur and phosphorus-substituted dienophiles and 2-aza-substituted 1,3-dienes

1984 ◽  
Vol 62 (11) ◽  
pp. 2089-2093 ◽  
Author(s):  
John M. McIntosh ◽  
Lilianna Z. Pillon
Keyword(s):  
Thermal Decomposition ◽  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Diels Alder Reaction

The use of 3-carboxylated 2,5-dihydrothiophenes as the dienophilic component of the Diels–Alder reaction has been investigated. The yields are generally quite low. The formation of conjugated dienes that are aminated at an interior position of the conjugated chain by formation and thermal decomposition of 3-acetamido-2,5-dihydrothiophenes appears to be a viable route to these useful compounds. One example of the Diels–Alder reaction of 2-carboxylated diethyl vinylphosphonates is reported.

A synthesis and some reactions of 7-Oxabicyclo[2.2.1]heptan-2-one

1983 ◽  
Vol 36 (12) ◽  
pp. 2473 ◽  
Author(s):  
J Moursounidis ◽  
D Wege
Keyword(s):  
Thermal Decomposition ◽  
Alder Reaction ◽  
Diels Alder ◽  
Acid Mixture ◽  
Diels Alder Reaction ◽  
Reaction Proceeds ◽  
Atom Migration ◽  
Acyl Azide ◽  
Mild Hydrolysis ◽  
Hydrolysis Of

Diels-Alder reaction between furan and α-chloroacrylonitrile gives a mixture of exo-2-chloro-and endo-2-chloro-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitrile (4) and (5). Mild hydrolysis affords the corresponding α-chloro acid mixture, from which the endo carboxylic acid may be removed through iodo lactone formation. Catalytic hydrogenation of (4) and (5) followed by hydrolysis, acyl azide formation, Curtius rearrangement, and hydrolysis of the resulting mixture of a-chloro isocyanates yields 7-oxabicyclo[2.2.l]heptan-2-one (1) in preparatively useful amounts. Reduction of (1) gives only endo alcohol, and Baeyer-Villiger reaction proceeds with exclusive bridgehead atom migration. Thermal decomposition of the sodium salt of the p-toluenesulfonylhydrazone of (1) affords 7-oxatricyclo[2.2.1 .02,6]heptane.

4-Aryl-3-substituted Furans

1994 ◽  
Vol 59 (12) ◽  
pp. 2721-2726 ◽  
Author(s):  
Jarmila Štetinová ◽  
Ján Leško ◽  
Miloslava Dandárová ◽  
Rudolf Kada ◽  
Roman Koreň
Keyword(s):  
Thermal Decomposition ◽  
Triple Bond ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Substituted Furans

4-Aryl-3-substituted furans IIIa - IIId were prepared by Diels Alder reaction of 4-phenyloxazole (I) with compounds IIa - IId, containing an activated triple bond, and subsequent thermal decomposition of the cycloadduct.

The synthesis, isomerization and stability of some enol-lactones

1982 ◽  
Vol 35 (9) ◽  
pp. 1903 ◽  
Author(s):  
IR Doyle ◽  
RA Massy-Westropp
Keyword(s):  
Thermal Decomposition ◽  
Wittig Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Kinetic Control ◽  
Relative Stabilities ◽  
Diels Alder Reaction ◽  
Wittig Reactions

The photoisomerization of enol-lactones is described. Thermal decomposition of (E) and (Z) ethyl 3-oxo-1,3,3aβ,4α,7α,7aβ-hexahydro-4,7-methanoisobenzofran-1-yideneacetates provides a good route to (E) and (Z) ethyl 5-oxo-2,5-dihydrofuran-2-ylideneacetates. Other examples of this retro-Diels-Alder reaction are reported. The relative stabilities of (E) and (Z) enol-lactones from the Wittig reaction between substituted succinic anhydrides and ethoxycarbonylmethylenetriphenylphosphorane have been determined. These Wittig reactions are under kinetic control.

Azadiene chemistry. 6. Competitive diene and dienophilic character of 2,3,4,5,5-pentachloro-1-azacyclopentadiene in Diels-Alder reaction with conjugated dienes

1981 ◽  
Vol 46 (15) ◽  
pp. 3036-3040 ◽  
Author(s):  
Bahlul K. Rammash ◽  
C. M. Gladstone ◽  
John L. Wong
Keyword(s):  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Diels Alder Reaction

scholarly journals Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

2016 ◽  
Vol 12 ◽  
pp. 1949-1980 ◽  
Author(s):  
Lucie Brulíková ◽  
Aidan Harrison ◽  
Marvin J Miller ◽  
Jan Hlaváč
Keyword(s):  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Conjugated Diene ◽  
Diels Alder Reaction ◽  
Oxazine Ring

The hetero-Diels–Alder reaction between a nitroso dienophile and a conjugated diene to give the 3,6-dihydro-2H-1,2-oxazine scaffold is useful for the synthesis of many biologically interesting molecules due to the diverse opportunities created by subsequent transformations of the resulting 1,2-oxazine ring. This review discusses the rationale for the observed regio- and stereoselectivity and the methods developed in recent years used to control and improve the stereo- and regioselectivity for the synthesis of 1,2-oxazine scaffolds.

scholarly journals Back Cover: Visible-Light, Photoredox-Mediated Oxidative Tandem Nitroso-Diels-Alder Reaction of Arylhydroxylamines with Conjugated Dienes (Eur. J. Org. Chem. 15/2017)

2017 ◽  
Vol 2017 (15) ◽  
pp. 2205-2205
Author(s):  
Veronica Santacroce ◽  
Raphael Duboc ◽  
Max Malacria ◽  
Giovanni Maestri ◽  
Geraldine Masson
Keyword(s):  
Visible Light ◽  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Back Cover ◽  
Diels Alder Reaction

The Aza Diels‐Alder Reaction on Brominated Conjugated Dienes.

2021 ◽  
Author(s):  
Rafael G. Uceda ◽  
Esther Roldan-Molina ◽  
Jorge A. R. Navarro ◽  
Juan Enrique Oltra
Keyword(s):  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Diels Alder Reaction

ChemInform Abstract: Hetero-Diels-Alder Reaction of Phosphinyl and Phosphonyl Nitroso Alkenes with Conjugated Dienes: An Aza-Cope Rearrangement.

ChemInform ◽  
2011 ◽  
Vol 42 (49) ◽  
pp. no-no
Author(s):  
Jesus M. de los Santos ◽  
Roberto Ignacio ◽  
Gloria Rubiales ◽  
Domitila Aparicio ◽  
Francisco Palacios
Keyword(s):  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Cope Rearrangement ◽  
Diels Alder Reaction
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