The title compound, C39H30OS, was inadvertently prepared as a Diels–Alder adduct between 1,3-diphenylisobenzofuran and 3-(1a,9b-dihydro-1H-cyclopropa[l]phenanthren-1-ylidene)tetrahydrothiophene. A combination of fused, bridged, and spirocyclic ring systems are all featured within a single molecular structure of this highly crowded polycyclic compound.
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Generation and Rearrangement of (1-Hydroxycyclopropyl)- and (1-Hydroxycyclobutyl)carbene
Photolysis of exo-1-(1a,9b-dihydro-1H-cyclopropa[l]phenanthren-1-yl)cyclopropan-1-ol and exo-1-(1a,9b-dihydro-1H-cyclopropa[l]phenanthren-1-yl)cyclobutan-1-ol in benzene-d6 produces (1-hydroxycyclopropyl)- and (1-hydroxycyclobutyl)carbene respectively. It was observed that (1-hydroxycyclopropyl)carbene rearranges to cyclobutanone whereas (1-hydroxycyclobutyl)carbene forms cyclopentanone. Formation of both ketones is attributed to tautomerization of the corresponding enols that arise from ring expansion of the carbenes. Products assignable to intramolecular C–H insertions were not detected in the photolysates.
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- Award ID(s):
- 1665278
- PAR ID:
- 10166485
- Date Published:
- Journal Name:
- Australian Journal of Chemistry
- Volume:
- 72
- Issue:
- 11
- ISSN:
- 0004-9425
- Page Range / eLocation ID:
- 890
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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