Next Article in Journal
Previous Article in Journal
1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid
Article Menu

Export Article

Open AccessCommunication
Molbank 2017, 2017(3), M948;


Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK
Author to whom correspondence should be addressed.
Received: 13 July 2017 / Revised: 25 July 2017 / Accepted: 31 July 2017 / Published: 1 August 2017
(This article belongs to the Section Organic Synthesis)
Full-Text   |   PDF [1083 KB, uploaded 1 August 2017]   |  


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. View Full-Text
Keywords: eucarvone; dimerization; cycloaddition; tosylhydrazone; 1,3-dipole; molecular rearrangement; Bamford-Stevens reaction eucarvone; dimerization; cycloaddition; tosylhydrazone; 1,3-dipole; molecular rearrangement; Bamford-Stevens reaction

Graphical abstract

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).

Supplementary materials


Share & Cite This Article

MDPI and ACS Style

Baumann, M.; Lapraille, S.; 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]. Molbank 2017, 2017, M948.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molbank EISSN 1422-8599 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top