Date of Award
Honors Thesis (Open Access)
Colby College. Chemistry Dept.
Dasan M. Thamattoor
Mundy, Bradford P.
2-(1a,9b-Dihydro-lH-cyclopropa[l]phenanthren-1-yl)-propan-2-ol was synthesized by two different but related synthetic routes and characterized by melting point, IR GC/MS, CHN, and NMR spectroscopy. Photolysis of the alcohol in benzene d-6 led to the formation of 2-butanone, 1-methylcyclopropanol, and 2,2-dimethyloxirane in a 26:10:1 ratio via 2-hydroxy-2methylpropylidene, a novel ?-hydroxycarbene. These products are a consequence of intramolecular insertions of the carbene into C-C, C-H, and O-H bonds. Molecular orbital calculations performed at the Becke-3LYP/6-31G(d) level indicate that the singlet form of this carbene is more thermodynamically stable than the triplet. Furthermore, the transition states to the three products from the singlet species were modeled at the same level of theory. Results from these computational studies are consistent with experimental observations.
Carbenes (Methylene compounds), Photochemistry, Organic compounds -- Synthesis, 2-hydroxy-2-methylpropylidene
Recommended CitationFarlow, Robin, "Photochemical generation and intramolecular chemistry of 2-hydroxy-2-methylpropylidene" (2001). Honors Theses. Paper 79.
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