ChemInform Abstract: ENTHALPY OF THE DIELS-ALDER REACTION OF CYCLOPENTADIEN AND MALEIC ANHYDRIDE

AbstractThe hetero-Diels-Alder reaction of 1-(2-furyl)-3-(dimethylamino)-2-propene-1-thione (diene) with maleic and fumaric acids, and β-nitrostyrenes yielded 3,4-dihydro-2H-thiopyran derivatives. Treatment of some of those cycloadducts with acetic acid caused elimination of dimethylamine yielding stable 2H-thiopyrans. Reaction of the diene with maleic anhydride furnished a cycloadduct which underwent spontaneous rearrangement to form an N,N-dimethylamide derivative. Cycloadditions of the diene to maleimide, N-phenylmaleimide, diethyl maleate, fumarate and butenolide, carried out in the presence of acetic anhydride,were followed by elimination of dimethylamine, afforded stable 2H-thiopyran derivatives.

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Reply to Comment on “Kinetics of a Diels−Alder Reaction of Maleic Anhydride and Isoprene in Supercritical CO2”

The Journal of Physical Chemistry A ◽

10.1021/jp030232v ◽

2003 ◽

Vol 107 (43) ◽

pp. 9249-9249 ◽

Cited By ~ 1

Author(s):

Evgeni M. Glebov ◽

Larisa G. Krishtopa ◽

Victor Stepanov ◽

Lev N. Krasnoperov

Keyword(s):

Maleic Anhydride ◽

Supercritical Co2 ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

Kinetics Of

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ChemInform Abstract: Alkatrienyl Sulfoxides and Sulfones. Part 8. Diels—Alder Reaction of 3-Methylpenta-1,2,4-trienyl Phenyl Sulfoxide with Maleic Anhydride.

ChemInform ◽

10.1002/chin.200808114 ◽

2008 ◽

Vol 39 (8) ◽

Author(s):

Valerji C. Christov ◽

Ivaylo K. Ivanov

Keyword(s):

Maleic Anhydride ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

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

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19930002773 ◽

1993 ◽

pp. 2773-2776 ◽

Cited By ~ 6

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

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The Diels-Alder Reaction with Maleic Anhydride

Organic Reactions ◽

10.1002/0471264180.or004.01 ◽

2011 ◽

pp. 1-59 ◽

Cited By ~ 3

Author(s):

Milton C. Kloetzel

Keyword(s):

Maleic Anhydride ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

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Vinylindenes and Some Heteroanalogs in the Diels-Alder Reaction. X. Dibenzofurans From 3-Vinylbenzofurans

Australian Journal of Chemistry ◽

10.1071/ch9911085 ◽

1991 ◽

Vol 44 (8) ◽

pp. 1085 ◽

Cited By ~ 12

Author(s):

JR Pearson ◽

QN Porter

Keyword(s):

Maleic Anhydride ◽

Alder Reaction ◽

Diels Alder ◽

Dimethyl Acetylenedicarboxylate ◽

Diels Alder Reaction

3-Vinylbenzofuran, 3-isopropenylbenzofuran and 2-methyl-3-vinylbenzofuran give normal [4π+2π] adducts with ethenetetracarbonitrile, accompanied, in the case of the last named diene, by the isomeric cyclobutane. Normal adducts also result from these dienes and 4-phenyl-1,2,4-triazoline-3,5-dione, and from 3-vinylbenzofuran and both maleic anhydride and N- phenylmaleimide. 3-Vinylbenzofuran gives the rearranged adduct dimethyl 1,2-dihydrodibenzofuran-3,4-dicarboxylate with dimethyl acetylenedicarboxylate.

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Vinylindenes and some heteroanalogues in the Diels-Alder reaction. II. Substituted fluorenes from 3-vinylindenes

Australian Journal of Chemistry ◽

10.1071/ch9771061 ◽

1977 ◽

Vol 30 (5) ◽

pp. 1061 ◽

Cited By ~ 4

Author(s):

R Bergamasco ◽

QN Porter

Keyword(s):

Mass Spectrometry ◽

Maleic Anhydride ◽

Alder Reaction ◽

Diels Alder ◽

Dimethyl Acetylenedicarboxylate ◽

Diels Alder Reaction

3-Vinylindene, 2-methyl-3-vinylindene and 3-isopropenylindene give normal, photostable adducts with ethenetetracarbonitrile by a Diels- Alder process. The first diene gives adducts with maleic anhydride, N- phenylmaleimide and dimethyl acetylenedicarboxylate. Where there is stereochemical ambiguity the adducts are shown by mass spectrometry to be exclusively endo. Two heterocyclic analogues are formed from 3- vinylindene with p-toluenesulphonyl cyanide and N-sulphinyl-p- toluenesulphonamide.

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