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

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...

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Veröffentlicht in:Organic letters 2024-05, Vol.26 (18), p.3840-3843
Hauptverfasser: Roth, Alexander D., Thamattoor, Dasan M.
Format: Artikel
Sprache:eng
Schlagworte:
Letter
phenol
trapping
traps
X-ray diffraction
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01001