(ƞ5-C5H5)Fe(CO)2(ƞ1-C5H5). A l

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

doi:10.1021/jo00191a005

(ƞ⁵-C₅H₅)Fe(CO)₂(ƞ¹-C₅H₅). A l

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

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

A variety of activated unsaturated compounds, including acrylonitrile, react with Fp(ƞ¹-C₅H₅), where Fp = (ƞ⁵-C₅H₅)Fe(CO)₂, to give cycloadducts in good yield. Diethylchloroalane facilitates these cycloadditions and even methyl acrylate cycloadds ingood yield in the presence of this Lewis acid. These reactions all occur regioandstereoselectively to afford syn-7-Fp cycloadducts exclusively. The stereochemistry at(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 carbonmonoxide saturated methanol. This two-step sequence, cycloaddition followed by oxidation, renders Fp(ƞ¹-C₅H₅) a synthetic equivalent of methyl 1,3-cyclopentadiene-5-carboxylate in cycloaddition reactions.

Original language	English (US)
Pages (from-to)	3059-3063
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	49
Issue number	17
DOIs	https://doi.org/10.1021/jo00191a005
State	Published - Nov 1984
Externally published	Yes

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Organic Chemistry

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title = "(ƞ5-C5H5)Fe(CO)2(ƞ1-C5H5). A l",

abstract = "A variety of activated unsaturated compounds, including acrylonitrile, react with Fp(ƞ1-C5H5), where Fp = (ƞ5-C5H5)Fe(CO)2, to give cycloadducts in good yield. Diethylchloroalane facilitates these cycloadditions and even methyl acrylate cycloadds ingood yield in the presence of this Lewis acid. These reactions all occur regioandstereoselectively to afford syn-7-Fp cycloadducts exclusively. The stereochemistry at(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 carbonmonoxide saturated methanol. This two-step sequence, cycloaddition followed by oxidation, renders Fp(ƞ1-C5H5) a synthetic equivalent of methyl 1,3-cyclopentadiene-5-carboxylate in cycloaddition reactions.",

author = "Wright, {Michael E.} and Hoover, {James F.} and Nelson, {Gregory O.} and Scott, {Carl P.} and Glass, {Richard S.}",

year = "1984",

month = nov,

doi = "10.1021/jo00191a005",

language = "English (US)",

volume = "49",

pages = "3059--3063",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

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T1 - (ƞ5-C5H5)Fe(CO)2(ƞ1-C5H5). A l

AU - Wright, Michael E.

AU - Hoover, James F.

AU - Nelson, Gregory O.

AU - Scott, Carl P.

AU - Glass, Richard S.

PY - 1984/11

Y1 - 1984/11

N2 - A variety of activated unsaturated compounds, including acrylonitrile, react with Fp(ƞ1-C5H5), where Fp = (ƞ5-C5H5)Fe(CO)2, to give cycloadducts in good yield. Diethylchloroalane facilitates these cycloadditions and even methyl acrylate cycloadds ingood yield in the presence of this Lewis acid. These reactions all occur regioandstereoselectively to afford syn-7-Fp cycloadducts exclusively. The stereochemistry at(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 carbonmonoxide saturated methanol. This two-step sequence, cycloaddition followed by oxidation, renders Fp(ƞ1-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(ƞ1-C5H5), where Fp = (ƞ5-C5H5)Fe(CO)2, to give cycloadducts in good yield. Diethylchloroalane facilitates these cycloadditions and even methyl acrylate cycloadds ingood yield in the presence of this Lewis acid. These reactions all occur regioandstereoselectively to afford syn-7-Fp cycloadducts exclusively. The stereochemistry at(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 carbonmonoxide saturated methanol. This two-step sequence, cycloaddition followed by oxidation, renders Fp(ƞ1-C5H5) a synthetic equivalent of methyl 1,3-cyclopentadiene-5-carboxylate in cycloaddition reactions.

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(ƞ⁵-C₅H₅)Fe(CO)₂(ƞ¹-C₅H₅). A l

Abstract

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