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.

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.

Citation

Baumann, M., & Baxendale, I. (2017). 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(3), Article M948. https://doi.org/10.3390/m948

• 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
• Electronic ISSN: 1422-8599
• 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