2. Academic Validation
  3. Formation and Rearrangement of a Congested Spiropentane from the Trapping of Dibenzonorcarynyliden(e/oid) by Phencyclone

Formation and Rearrangement of a Congested Spiropentane from the Trapping of Dibenzonorcarynyliden(e/oid) by Phencyclone

  • Org Lett. 2024 May 10;26(18):3840-3843. doi: 10.1021/acs.orglett.4c01001.
Alexander D Roth 1,  Dasan M Thamattoor 1
Affiliations

Affiliation

  • 1 Department of Chemistry, Colby College, Waterville, Maine 04901, United States.
PMID: 38669627 DOI: 10.1021/acs.orglett.4c01001
Abstract

The low-temperature treatment of 1,1-dibromo-1a,9b-cyclopropa[l]phenanthrene with butyllithium appeared to produce dibenzonorcarynyliden(e/oid) which could be intercepted with phencyclone to produce a hindered spiropentane. The spiropentane readily rearranges, thermally and photochemically, into a triphenylene phenol derivative. The spiropentane and its rearrangement product were characterized by X-ray crystallography.

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