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Open AccessCommunication
Molbank 2017, 2017(3), M948; doi:10.3390/M948

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]

Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK
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Received: 13 July 2017 / Revised: 25 July 2017 / Accepted: 31 July 2017 / Published: 1 August 2017
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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. 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
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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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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.

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