5-C5H5)Fe(CO)21-C5H5). A useful synthetic equivalent of methyl 1,3-cyclopentadiene-5-carboxylate in cycloaddition reactions

Michael E. Wright, James F. Hoover, Gregory O. Nelson, Carl P. Scott, Richard S. Glass

Research output: Research - peer-reviewArticle

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Abstract

A variety of activated unsaturated compounds, including acrylonitrile, react with Fp(η1-C5H5), where Fp = (η5-C5H5)Fe(CO)2, to give cycloadducts in good yield. Diethylchloroalane facilitates these cycloadditions and even methyl acrylate cycloadds in good yield in the presence of this Lewis acid. These reactions all occur regio-and stereoselectively to afford syn-7-Fp cycloadducts exclusively. The stereochemistry at C(2) and C(3) is selective in some cases but not in others. Stereospecific replacement of the Fp moiety in these cycloadducts by a CO2Me group with retention of configuration occurs in good yield by oxidation with ammonium cerium(IV) nitrate in carbon monoxide saturated methanol. This two-step sequence, cycloaddition followed by oxidation, renders Fp(η1-C5H5) a synthetic equivalent of methyl 1,3-cyclopentadiene-5-carboxylate in cycloaddition reactions.

LanguageEnglish (US)
Pages3059-3063
Number of pages5
JournalJournal of Organic Chemistry
Volume49
Issue number17
StatePublished - 1984

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1,3-cyclopentadiene
Oxidation
Unsaturated compounds
Acrylonitrile
Lewis Acids
Methanol
methyl acrylate
cerium(IV) ammonium nitrate

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

5-C5H5)Fe(CO)21-C5H5). A useful synthetic equivalent of methyl 1,3-cyclopentadiene-5-carboxylate in cycloaddition reactions. / Wright, Michael E.; Hoover, James F.; Nelson, Gregory O.; Scott, Carl P.; Glass, Richard S.

In: Journal of Organic Chemistry, Vol. 49, No. 17, 1984, p. 3059-3063.

Research output: Research - peer-reviewArticle

Wright, Michael E. ; Hoover, James F. ; Nelson, Gregory O. ; Scott, Carl P. ; Glass, Richard S./ 5-C5H5)Fe(CO)21-C5H5). A useful synthetic equivalent of methyl 1,3-cyclopentadiene-5-carboxylate in cycloaddition reactions. In: Journal of Organic Chemistry. 1984 ; Vol. 49, No. 17. pp. 3059-3063
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abstract = "A variety of activated unsaturated compounds, including acrylonitrile, react with Fp(η1-C5H5), where Fp = (η5-C5H5)Fe(CO)2, to give cycloadducts in good yield. Diethylchloroalane facilitates these cycloadditions and even methyl acrylate cycloadds in good yield in the presence of this Lewis acid. These reactions all occur regio-and stereoselectively to afford syn-7-Fp cycloadducts exclusively. The stereochemistry at C(2) and C(3) is selective in some cases but not in others. Stereospecific replacement of the Fp moiety in these cycloadducts by a CO2Me group with retention of configuration occurs in good yield by oxidation with ammonium cerium(IV) nitrate in carbon monoxide saturated methanol. This two-step sequence, cycloaddition followed by oxidation, renders Fp(η1-C5H5) a synthetic equivalent of methyl 1,3-cyclopentadiene-5-carboxylate in cycloaddition reactions.",
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AU - Hoover,James F.

AU - Nelson,Gregory O.

AU - Scott,Carl P.

AU - Glass,Richard S.

PY - 1984

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N2 - A variety of activated unsaturated compounds, including acrylonitrile, react with Fp(η1-C5H5), where Fp = (η5-C5H5)Fe(CO)2, to give cycloadducts in good yield. Diethylchloroalane facilitates these cycloadditions and even methyl acrylate cycloadds in good yield in the presence of this Lewis acid. These reactions all occur regio-and stereoselectively to afford syn-7-Fp cycloadducts exclusively. The stereochemistry at C(2) and C(3) is selective in some cases but not in others. Stereospecific replacement of the Fp moiety in these cycloadducts by a CO2Me group with retention of configuration occurs in good yield by oxidation with ammonium cerium(IV) nitrate in carbon monoxide saturated methanol. This two-step sequence, cycloaddition followed by oxidation, renders Fp(η1-C5H5) a synthetic equivalent of methyl 1,3-cyclopentadiene-5-carboxylate in cycloaddition reactions.

AB - A variety of activated unsaturated compounds, including acrylonitrile, react with Fp(η1-C5H5), where Fp = (η5-C5H5)Fe(CO)2, to give cycloadducts in good yield. Diethylchloroalane facilitates these cycloadditions and even methyl acrylate cycloadds in good yield in the presence of this Lewis acid. These reactions all occur regio-and stereoselectively to afford syn-7-Fp cycloadducts exclusively. The stereochemistry at C(2) and C(3) is selective in some cases but not in others. Stereospecific replacement of the Fp moiety in these cycloadducts by a CO2Me group with retention of configuration occurs in good yield by oxidation with ammonium cerium(IV) nitrate in carbon monoxide saturated methanol. This two-step sequence, cycloaddition followed by oxidation, renders Fp(η1-C5H5) a synthetic equivalent of methyl 1,3-cyclopentadiene-5-carboxylate in cycloaddition reactions.

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