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Rac-2′,3a,6,6,6′,6′-Hexamethyl-3a,3b,6,7-tetra-hydrospiro-[benzo[2,3]cyclopropa[1,2-c]pyrazole-1,1′-cyclo-hepta[2,4]diene]

Baumann, M.; Baxendale, I.R.

Rac-2′,3a,6,6,6′,6′-Hexamethyl-3a,3b,6,7-tetra-hydrospiro-[benzo[2,3]cyclopropa[1,2-c]pyrazole-1,1′-cyclo-hepta[2,4]diene] Thumbnail


Authors

M. Baumann



Abstract

This note describes a novel reaction cascade in which a tosylhydrazone derivative of eucarvone undergoes a non-classical dimerization process under basic conditions. The key step in this sequence is a dipolar cycloaddition between a diazo species and a transient cyclopropene. A proposed mechanism for this sequence is presented that is supported by single crystal X-ray analysis of the resulting dimer. We believe this unique transformation is of note as it highlights a neat and efficient entry to complex polycyclic architectures containing an embedded pyrazoline moiety.

Journal Article Type Article
Acceptance Date Jul 31, 2017
Online Publication Date Aug 1, 2017
Publication Date Aug 1, 2017
Deposit Date Aug 2, 2017
Publicly Available Date Aug 2, 2017
Journal Molbank
Publisher MDPI
Peer Reviewed Peer Reviewed
Volume 2017
Issue 3
Article Number M948
DOI https://doi.org/10.3390/m948
Public URL https://durham-repository.worktribe.com/output/1380095

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Copyright Statement
© 2017 by the authors. Licensee MDPI, Basel, Switzerland. This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).





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