Amidation of deltacyclene and hexacyclic norbornadiene dimers with acetonitrile and water catalyzed by FeCl₃·6H₂O

Abstract

FeCl₃·6H₂O-catalyzed Ritter amidation of deltacyclene and hexacyclic norbornadiene dimers containing both a double bond and a three-carbon ring in the molecule with acetonitrile and water was performed. Depending on the hydrocarbon structure, the reaction proceeds via C-C bond cleavage in the three-carbon ring or at the double bond to form the corresponding N-acetamides.

GRAPHICAL ABSTRACT

Keywords:

• Acetonitrile
• amidation
• deltacyclene
• hexacyclo[9.2.1.0.2100.380.46059]tetradec-12-enes
• iron(III) chloride hexahydrate

Acknowledgments

This study was performed using research equipment of the Regional Center for Collective Use “Agidel”.

Additional information

Funding

This study was performed within the state assignment (Reg. No. АААА-А19-11902229009-3) and was supported by the Russian Foundation for Basic Research (RFBR No.17-43-020561 p_povolzhie_a).