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Title: 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.  more » « less
Award ID(s):
1665278
NSF-PAR ID:
10166485
Author(s) / Creator(s):
; ;
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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