5-C5H5)Fe(CO)21-C5R5). A Useful Synthetic Equivalent of 5-Amino-1,3-cyclopentadiene in Cycloaddition Reactions

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

Research output: Contribution to journalArticle

10 Scopus citations

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 (n5-C5H5)Fe-(CO)2(n1-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 (n5-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.

Original languageEnglish (US)
Pages (from-to)5123-5127
Number of pages5
JournalJournal of Organic Chemistry
Volume51
Issue number26
DOIs
StatePublished - Jan 1 1986

ASJC Scopus subject areas

  • Organic Chemistry

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