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1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid
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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]

Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK
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Molbank 2017, 2017(3), M948; https://doi.org/10.3390/M948
Received: 13 July 2017 / Revised: 25 July 2017 / Accepted: 31 July 2017 / Published: 1 August 2017
(This article belongs to the Section Organic Synthesis)
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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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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