Structural Chemistry

, Volume 29, Issue 5, pp 1511–1523 | Cite as

A theoretical investigation on the mechanism of cycloaddition reactions of fulvenes with tetrazine and diazacyclopentadienone derivatives

  • Mina Haghdadi
  • Mina Alashti
  • Hassan Ghasemnejad Bosra
Original Research


The mechanism of cycloaddition reactions for 6-dimethylaminofulvene and 6,6-diphenylfulvene with tetrazine and diazacyclopentadienone are studied by DFT at the MPWB1K/cc-pVDZ level of theory. The energy results indicated that the [6 + 4] cycloaddition reaction of 6-dimethylaminofulvene with tetrazine and diazacyclopentadienone derivatives proceeds in a stepwise fashion, while the [2 + 4] cycloaddition reaction of 6,6-diphenylfulvene might proceed in a one-step fashion. Our calculations showed some unfavorable processes with unstable cycloadducts arising from [4 + 2] cycloaddition reactions which are unobserved in the experimental results. Also, an analysis of the Parr functions for the reactants allows us to provide an explanation of the selectivity of these cycloaddition reactions.


Cycloaddition reactions One-step Stepwise Fulvene Density functional theory Domino reaction 



The authors wish to acknowledge Dr. Louise S. Price, University College London, UK, for reading the manuscript and providing valuable suggestions.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Ethical responsibilities of authors

We warranty that this manuscript is original, that this has been written by the stated authors, and that this has not been published elsewhere; the manuscript has not been submitted to more than one journal for simultaneous consideration.

We wish to confirm that it has not been published previously (partly or in full). This study is not split-up into several parts. We confirm that no data have been fabricated or manipulated. No data, text, or theories by others are presented as if they were the authors property. This manuscript contains no libelous or other unlawful statements and does not contain any materials that violate any personal or proprietary rights of any other person or entity.

Supplementary material

11224_2018_1138_MOESM1_ESM.docx (448 kb)
ESM 1 (DOCX 448 kb)


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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Mina Haghdadi
    • 1
  • Mina Alashti
    • 1
  • Hassan Ghasemnejad Bosra
    • 1
  1. 1.Department of ChemistryIslamic Azad UniversityBabolIran

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