Synthesis of New Ferrocenyl‐Substituted Aziridines via the Gabriel–Cromwell Reaction

Abstract

The Gabriel–Cromwell method is applied successfully in the synthesis of ferrocenyl‐substituted aziridines. Acryloyl‐ and crotonoylferrocenes are brominated first and then reacted with benzylamine, diisopropylamine, and furfurylamine in the presence of triethylamine. The aziridines are obtained in more than 90% isolated yields.

Keywords:

• α‐Bromoacryloyferrocene
• α‐bromocrotonoylferrocene
• aziridines
• ferrocenylenones
• Gabriel–Cromwell method

Acknowledgments

We thank the Scientific and Technical Research Council of Turkey (TUBITAK, Grant No. TBAG‐ U/57, 102T214), the Middle East Technical University, and Kırıkkale University Research Foundations for financial support.

Notes

^†Crystallographic data for structure of 8a‐ trans have been deposited with the CCDC as supplementary publication no. CCDC 248289. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44‐ 1223‐336‐033; E‐mail: [email protected]. uk).