We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Generation and Rearrangement of (1-Hydroxycyclopropyl)- and (1-Hydroxycyclobutyl)carbene.
- Authors
DeAngelo, Joseph D.; Hatano, Sayaka; Thamattoor, Dasan M.
- Abstract
Photolysis of exo -1-(1 a ,9 b -dihydro-1 H -cyclopropa[ l ]phenanthren-1-yl)cyclopropan-1-ol and exo -1-(1 a ,9 b -dihydro-1 H -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. Two cyclopropanated phenanthrene derivatives have been synthesized and photolyzed in solution to produce (1-hydroxycyclopropyl)- and (1-hydroxycyclobutyl)carbene. The carbenes rearrange by ring expansion.
- Subjects
PHENANTHRENE derivatives; ENOLS; PHENANTHRENE; KETONES; REPRODUCTION
- Publication
Australian Journal of Chemistry, 2019, Vol 72, Issue 11, p890
- ISSN
0004-9425
- Publication type
Article
- DOI
10.1071/CH19379