Date of Award
Honors Thesis (Open Access)
Colby College. Chemistry Dept.
Dasan M. Thamattoor
Jeffrey L. Katz
2-methoxy-2-methylpropylidene was photochemically generated from a non-nitrogenous precursor, 1a,9b-Dihydro-IH-cyclopropaphenanthrene-l-etbane 2-methoxy-2-methyl, available in two steps from phenanthrene. Two competing rearrangement pathways were observed for the p-methoxy carbene, 1,2-methyl shift and C-H insertion, which had varying weights depending on the solvent used. Nevertheless, the C-H insertion was always predominant, contrary to the current understanding of B-substituted carbenes, which apparently needs revision. An attempt was also made to measure by LFP the rate constant of rearrangement and lifetime of the stabilized l-chloro-2-methoxy-2-metbylpropylidene.
Carbenes (Methylene compounds), Photochemistry, Organic compounds -- Synthesis, 2-methoxy-2-methylpropylidene
Recommended CitationPresolski, Stanislav, "Photochemical generation of 2-methoxy-2methylpropylidene and its rearrangement pathways" (2005). Honors Theses. Paper 201.
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