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

Richard S. Glass, Wesley W. McConnell, Stephen W. Andruski

Research output: Research - peer-reviewArticle

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Abstract

Diels-Alder reactions of 5-amino-1,3-cyclopentadiene have not been reported, and other stereoselective, high-yield routes to substituted bicyclo[2.2.1]hept-2-en-7-syn-amines are limited. This paper reports use of (η5-C6H5)Fe-(CO)21-C5H5) (1) as a synthetic equivalent of 5-amino-1,3-cyclopentadiene in cycloaddition reactions. The previously reported cycloadducts of 1 and alkenes were treated with ammonium cerium(IV) nitrate, bromine, or chlorine in acetonitrile containing sodium azide to give the corresponding acyl azides in which the CON3 group replaced the (η5-C5H5)Fe(CO)2 group with retention of stereochemistry in good yield. Thermal Curtius rearrangement of these acyl azides proceeded stereospecifically in excellent yield. This regioselective and stereoselective sequence provides a useful route to substituted 7-syn-amino-2-norbornenes.

LanguageEnglish (US)
Pages5123-5127
Number of pages5
JournalJournal of Organic Chemistry
Volume51
Issue number26
StatePublished - 1986

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Azides
1,3-cyclopentadiene
Sodium Azide
Chlorine
Alkenes
Amines
Hot Temperature
acetonitrile
cerium(IV) ammonium nitrate

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

5-C5H5)Fe(CO)21-C5H5). A useful synthetic equivalent of 5-amino-1,3-cyclopentadiene in cycloaddition reactions. / Glass, Richard S.; McConnell, Wesley W.; Andruski, Stephen W.

In: Journal of Organic Chemistry, Vol. 51, No. 26, 1986, p. 5123-5127.

Research output: Research - peer-reviewArticle

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abstract = "Diels-Alder reactions of 5-amino-1,3-cyclopentadiene have not been reported, and other stereoselective, high-yield routes to substituted bicyclo[2.2.1]hept-2-en-7-syn-amines are limited. This paper reports use of (η5-C6H5)Fe-(CO)2(η 1-C5H5) (1) as a synthetic equivalent of 5-amino-1,3-cyclopentadiene in cycloaddition reactions. The previously reported cycloadducts of 1 and alkenes were treated with ammonium cerium(IV) nitrate, bromine, or chlorine in acetonitrile containing sodium azide to give the corresponding acyl azides in which the CON3 group replaced the (η5-C5H5)Fe(CO)2 group with retention of stereochemistry in good yield. Thermal Curtius rearrangement of these acyl azides proceeded stereospecifically in excellent yield. This regioselective and stereoselective sequence provides a useful route to substituted 7-syn-amino-2-norbornenes.",
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AU - McConnell,Wesley W.

AU - Andruski,Stephen W.

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N2 - Diels-Alder reactions of 5-amino-1,3-cyclopentadiene have not been reported, and other stereoselective, high-yield routes to substituted bicyclo[2.2.1]hept-2-en-7-syn-amines are limited. This paper reports use of (η5-C6H5)Fe-(CO)2(η 1-C5H5) (1) as a synthetic equivalent of 5-amino-1,3-cyclopentadiene in cycloaddition reactions. The previously reported cycloadducts of 1 and alkenes were treated with ammonium cerium(IV) nitrate, bromine, or chlorine in acetonitrile containing sodium azide to give the corresponding acyl azides in which the CON3 group replaced the (η5-C5H5)Fe(CO)2 group with retention of stereochemistry in good yield. Thermal Curtius rearrangement of these acyl azides proceeded stereospecifically in excellent yield. This regioselective and stereoselective sequence provides a useful route to substituted 7-syn-amino-2-norbornenes.

AB - Diels-Alder reactions of 5-amino-1,3-cyclopentadiene have not been reported, and other stereoselective, high-yield routes to substituted bicyclo[2.2.1]hept-2-en-7-syn-amines are limited. This paper reports use of (η5-C6H5)Fe-(CO)2(η 1-C5H5) (1) as a synthetic equivalent of 5-amino-1,3-cyclopentadiene in cycloaddition reactions. The previously reported cycloadducts of 1 and alkenes were treated with ammonium cerium(IV) nitrate, bromine, or chlorine in acetonitrile containing sodium azide to give the corresponding acyl azides in which the CON3 group replaced the (η5-C5H5)Fe(CO)2 group with retention of stereochemistry in good yield. Thermal Curtius rearrangement of these acyl azides proceeded stereospecifically in excellent yield. This regioselective and stereoselective sequence provides a useful route to substituted 7-syn-amino-2-norbornenes.

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