Unusual rearrangement in the reaction of cyclopropanated cyclopentadienes with Et₃Al/CH₂I₂ in CH₂Cl₂

Abstract

The reaction of Et₃Al/CH₂I₂ reagent with cyclopropanated spiro[2.4]hepta-4,6-diene and 6-substituted fulvenes in CH₂Cl₂ was found to lead to the selective formation of rearrangement products through sequential cyclopropyl-allyl rearrangement and cyclopropanation.

Graphical Abstrat

Keywords:

• Aluminum carbenoids
• cyclopropanation
• cyclopropyl-allyl rearrangement
• fulvenes
• polycyclopropanes
• spiro[2,4]hepta-4,6-diene

Acknowledgments

We acknowledge the Institute of Petrochemistry and Catalysis of the Russian Academy of Sciences for allowing collective use of unique equipments «Agidel».

Additional information

Funding

This work was supported by the program of the Presidium of the Russian Academy of Sciences No. 38 “The study of the fundamental problems of synthesis and ‘structure-property’ dependence to create new substances and materials” and the Ministry of Science and Education of the Russian Federation (NSh-5240.2018.3).